Dr. Laurie Starkey

Organic Synthesis Strategies

Slide Duration:

Table of Contents

Section 1: Introduction to Organic Molecules

Introduction and Drawing Structures

49m 51s

Intro

0:00

Organic Chemistry

0:07

Organic

0:08

Inorganic

0:26

Examples of Organic Compounds

1:16

Review Some Chemistry Basics

5:23

Electrons

5:42

Orbitals (s,p,d,f)

6:12

Review Some Chemistry Basics

7:35

Elements & Noble Gases

7:36

Atom & Valance Shell

8:47

Review Some Chemistry Basics

11:33

Electronegative Elements

11:34

Which Is More Electronegative, C or N?

13:45

Ionic & Covalent Bonds

14:07

Ionic Bonds

14:08

Covalent Bonds

16:17

Polar Covalent Bonds

19:35

Polar Covalent Bonds & Electronegativities

19:37

Polarity of Molecules

22:56

Linear molecule

23:07

Bent Molecule

23:53

No Polar Bonds

24:21

Ionic

24:52

Line Drawings

26:36

Line Drawing Overview

26:37

Line Drawing: Example 1

27:12

Line Drawing: Example 2

29:14

Line Drawing: Example 3

29:51

Line Drawing: Example 4

30:34

Line Drawing: Example 5

31:21

Line Drawing: Example 6

32:41

Diversity of Organic Compounds

33:57

Diversity of Organic Compounds

33:58

Diversity of Organic Compounds, cont.

39:16

Diversity of Organic Compounds, cont.

39:17

Examples of Polymers

45:26

Examples of Polymers

45:27

Lewis Structures & Resonance

44m 25s

Intro

0:00

Lewis Structures

0:08

How to Draw a Lewis Structure

0:09

Examples

2:20

Lewis Structures

6:25

Examples: Lewis Structure

6:27

Determining Formal Charges

8:48

Example: Determining Formal Charges for Carbon

10:11

Example: Determining Formal Charges for Oxygen

11:02

Lewis Structures

12:08

Typical, Stable Bonding Patterns: Hydrogen

12:11

Typical, Stable Bonding Patterns: Carbon

12:58

Typical, Stable Bonding Patterns: Nitrogen

13:25

Typical, Stable Bonding Patterns: Oxygen

13:54

Typical, Stable Bonding Patterns: Halogen

14:16

Lewis Structure Example

15:17

Drawing a Lewis Structure for Nitric Acid

15:18

Resonance

21:58

Definition of Resonance

22:00

Delocalization

22:07

Hybrid Structure

22:38

Rules for Estimating Stability of Resonance Structures

26:04

Rule Number 1: Complete Octets

26:10

Rule Number 2: Separation of Charge

28:13

Rule Number 3: Negative and Positive Charges

30:02

Rule Number 4: Equivalent

31:06

Looking for Resonance

32:09

Lone Pair Next to a p Bond

32:10

Vacancy Next to a p Bond

33:53

p Bond Between Two Different Elements

35:00

Other Type of Resonance: Benzene

36:06

Resonance Example

37:29

Draw and Rank Resonance Forms

37:30

Acid-Base Reactions

1h 7m 46s

Intro

0:00

Acid-Base Reactions

0:07

Overview

0:08

Lewis Acid and Lewis Base

0:30

Example 1: Lewis Acid and Lewis Base

1:53

Example 2: Lewis Acid and Lewis Base

3:04

Acid-base Reactions

4:54

Bonsted-Lowry Acid and Bonsted-Lowry Base

4:56

Proton Transfer Reaction

5:36

Acid-Base Equilibrium

8:14

Two Acids in Competition = Equilibrium

8:15

Example: Which is the Stronger Acid?

8:40

Periodic Trends for Acidity

12:40

Across Row

12:41

Periodic Trends for Acidity

19:48

Energy Diagram

19:50

Periodic Trends for Acidity

21:28

Down a Family

21:29

Inductive Effects on Acidity

25:52

Example: Which is the Stronger Acid?

25:54

Other Electron-Withdrawing Group (EWG)

30:37

Inductive Effects on Acidity

32:55

Inductive Effects Decrease with Distance

32:56

Resonance Effects on Acidity

36:35

Examples of Resonance Effects on Acidity

36:36

Resonance Effects on Acidity

41:15

Small and Large Amount of Resonance

41:17

Acid-Base Example

43:10

Which is Most Acidic? Which is the Least Acidic?

43:12

Acid-Base Example

49:26

Which is the Stronger Base?

49:27

Acid-Base Example

53:58

Which is the Strongest Base?

53:59

Common Acids/Bases

1:00:45

Common Acids/Bases

1:00:46

Example: Determine the Direction of Equilibrium

1:04:51

Structures and Properties of Organic Molecules

1h 23m 35s

Intro

0:00

Orbitals and Bonding

0:20

Atomic Orbitals (AO)

0:21

Molecular Orbitals (MO)

1:46

Definition of Molecular Orbitals

1:47

Example 1: Formation of Sigma Bond and Molecular Orbitals

2:20

Molecular Orbitals (MO)

5:25

Example 2: Formation of Pi Bond

5:26

Overlapping E Levels of MO's

7:28

Energy Diagram

7:29

Electronic Transitions

9:18

Electronic Transitions

9:23

Hybrid Orbitals

12:04

Carbon AO

12:06

Hybridization

13:51

Hybrid Orbitals

15:02

Examples of Hybrid Orbitals

15:05

Example: Assign Hybridization

20:31

3-D Sketches

24:05

sp3

24:24

sp2

25:28

27:41

3-D Sketches of Molecules

29:07

3-D Sketches of Molecules 1

29:08

3-D Sketches of Molecules 2

32:29

3-D Sketches of Molecules 3

35:36

3D Sketch

37:20

How to Draw 3D Sketch

37:22

Example 1: Drawing 3D Sketch

37:50

Example 2: Drawing 3D Sketch

43:04

Hybridization and Resonance

46:06

Example: Hybridization and Resonance

46:08

Physical Properties

49:55

Water Solubility, Boiling Points, and Intermolecular Forces

49:56

Types of 'Nonbonding' Interactions

51:47

Dipole-Dipole

52:37

Definition of Dipole-Dipole

52:39

Example: Dipole-Dipole Bonding

53:27

Hydrogen Bonding

57:14

Definition of Hydrogen Bonding

57:15

Example: Hydrogen Bonding

58:05

Van Der Waals/ London Forces

1:03:11

Van Der Waals/ London Forces

1:03:12

Example: Van Der Waals/ London Forces

1:04:59

Water Solubility

1:08:32

Water Solubility

1:08:34

Example: Water Solubility

1:09:05

Example: Acetone

1:11:29

Isomerism

1:13:51

Definition of Isomers

1:13:53

Constitutional Isomers and Example

1:14:17

Stereoisomers and Example

1:15:34

Introduction to Functional Groups

1:17:06

Functional Groups: Example, Abbreviation, and Name

1:17:07

Introduction to Functional Groups

1:20:48

Functional Groups: Example, Abbreviation, and Name

1:20:49

Alkane Structures

1h 13m 38s

Intro

0:00

Nomenclature of Alkanes

0:12

Nomenclature of Alkanes and IUPAC Rules

0:13

Examples: Nomenclature of Alkanes

4:38

Molecular Formula and Degrees of Unsaturation (DU)

17:24

Alkane Formula

17:25

Example: Heptane

17:58

Why '2n+2' Hydrogens?

18:35

Adding a Ring

19:20

Adding a p Bond

19:42

Example 1: Determine Degrees of Unsaturation (DU)

20:17

Example 2: Determine Degrees of Unsaturation (DU)

21:35

Example 3: Determine DU of Benzene

23:30

Molecular Formula and Degrees of Unsaturation (DU)

24:41

Example 4: Draw Isomers

24:42

Physical properties of Alkanes

29:17

Physical properties of Alkanes

29:18

Conformations of Alkanes

33:40

Conformational Isomers

33:42

Conformations of Ethane: Eclipsed and Staggered

34:40

Newman Projection of Ethane

36:15

Conformations of Ethane

40:38

Energy and Degrees Rotated Diagram

40:41

Conformations of Butane

42:28

Butane

42:29

Newman Projection of Butane

43:35

Conformations of Butane

44:25

Energy and Degrees Rotated Diagram

44:30

Cycloalkanes

51:26

Cyclopropane and Cyclobutane

51:27

Cyclopentane

53:56

Cycloalkanes

54:56

Cyclohexane: Chair, Boat, and Twist Boat Conformations

54:57

Drawing a Cyclohexane Chair

57:58

Drawing a Cyclohexane Chair

57:59

Newman Projection of Cyclohexane

1:02:14

Cyclohexane Chair Flips

1:04:06

Axial and Equatorial Groups

1:04:10

Example: Chair Flip on Methylcyclohexane

1:06:44

Cyclohexane Conformations Example

1:09:01

Chair Conformations of cis-1-t-butyl-4-methylcyclohexane

1:09:02

Stereochemistry

1h 40m 54s

Intro

0:00

Stereochemistry

0:10

Isomers

0:11

Stereoisomer Examples

1:30

Alkenes

1:31

Cycloalkanes

2:35

Stereoisomer Examples

4:00

Tetrahedral Carbon: Superimposable (Identical)

4:01

Tetrahedral Carbon: Non-Superimposable (Stereoisomers)

5:18

Chirality

7:18

Stereoisomers

7:19

Chiral

8:05

Achiral

8:29

Example: Achiral and Chiral

8:45

Chirality

20:11

Superimposable, Non-Superimposable, Chiral, and Achiral

20:12

Nomenclature

23:00

Cahn-Ingold-Prelog Rules

23:01

Nomenclature

29:39

Example 1: Nomenclature

29:40

Example 2: Nomenclature

31:49

Example 3: Nomenclature

33:24

Example 4: Nomenclature

35:39

Drawing Stereoisomers

36:58

Drawing (S)-2-bromopentane

36:59

Drawing the Enantiomer of (S)-2-bromopentane: Method 1

38:47

Drawing the Enantiomer of (S)-2-bromopentane: Method 2

39:35

Fischer Projections

41:47

Definition of Fischer Projections

41:49

Drawing Fischer Projection

43:43

Use of Fisher Projection: Assigning Configuration

49:13

Molecules with Two Chiral Carbons

51:49

Example A

51:42

Drawing Enantiomer of Example A

53:26

Fischer Projection of A

54:25

Drawing Stereoisomers, cont.

59:40

Drawing Stereoisomers Examples

59:41

Diastereomers

1:01:48

Drawing Stereoisomers

1:06:37

Draw All Stereoisomers of 2,3-dichlorobutane

1:06:38

Molecules with Two Chiral Centers

1:10:22

Draw All Stereoisomers of 2,3-dichlorobutane, cont.

1:10:23

Optical Activity

1:14:10

Chiral Molecules

1:14:11

Angle of Rotation

1:14:51

Achiral Species

1:16:46

Physical Properties of Stereoisomers

1:17:11

Enantiomers

1:17:12

Diastereomers

1:18:01

Example

1:18:26

Physical Properties of Stereoisomers

1:23:05

When Do Enantiomers Behave Differently?

1:23:06

Racemic Mixtures

1:28:18

Racemic Mixtures

1:28:21

Resolution

1:29:52

Unequal Mixtures of Enantiomers

1:32:54

Enantiomeric Excess (ee)

1:32:55

Unequal Mixture of Enantiomers

1:34:43

Unequal Mixture of Enantiomers

1:34:44

Example: Finding ee

1:36:38

Example: Percent of Composition

1:39:46

Section 2: Understanding Organic Reactions

Nomenclature

1h 53m 47s

Intro

0:00

Cycloalkane Nomenclature

0:17

Cycloalkane Nomenclature and Examples

0:18

Alkene Nomenclature

6:28

Alkene Nomenclature and Examples

6:29

Alkene Nomenclature: Stereochemistry

15:07

Alkenes With Two Groups: Cis & Trans

15:08

Alkenes With Greater Than Two Groups: E & Z

18:26

Alkyne Nomenclature

24:46

Alkyne Nomenclature and Examples

24:47

Alkane Has a Higher Priority Than Alkyne

28:25

Alcohol Nomenclature

29:24

Alcohol Nomenclature and Examples

29:25

Alcohol FG Has Priority Over Alkene/yne

33:41

Ether Nomenclature

36:32

Ether Nomenclature and Examples

36:33

Amine Nomenclature

42:59

Amine Nomenclature and Examples

43:00

Amine Nomenclature

49:45

Primary, Secondary, Tertiary, Quaternary Salt

49:46

Aldehyde Nomenclature

51:37

Aldehyde Nomenclature and Examples

51:38

Ketone Nomenclature

58:43

Ketone Nomenclature and Examples

58:44

Aromatic Nomenclature

1:05:02

Aromatic Nomenclature and Examples

1:05:03

Aromatic Nomenclature, cont.

1:09:09

Ortho, Meta, and Para

1:09:10

Aromatic Nomenclature, cont.

1:13:27

Common Names for Simple Substituted Aromatic Compounds

1:13:28

Carboxylic Acid Nomenclature

1:16:35

Carboxylic Acid Nomenclature and Examples

1:16:36

Carboxylic Acid Derivatives

1:22:28

Carboxylic Acid Derivatives

1:22:42

General Structure

1:23:10

Acid Halide Nomenclature

1:24:48

Acid Halide Nomenclature and Examples

1:24:49

Anhydride Nomenclature

1:28:10

Anhydride Nomenclature and Examples

1:28:11

Ester Nomenclature

1:32:50

Ester Nomenclature

1:32:51

Carboxylate Salts

1:38:51

Amide Nomenclature

1:40:02

Amide Nomenclature and Examples

1:40:03

Nitrile Nomenclature

1:45:22

Nitrile Nomenclature and Examples

1:45:23

Chemical Reactions

51m 1s

Intro

0:00

Chemical Reactions

0:06

Reactants and Products

0:07

Thermodynamics

0:50

Equilibrium Constant

1:06

Equation

2:35

Organic Reaction

3:05

Energy vs. Progress of Rxn Diagrams

3:48

Exothermic Reaction

4:02

Endothermic Reaction

6:54

Estimating ΔH rxn

9:15

Bond Breaking

10:03

Bond Formation

10:25

Bond Strength

11:35

Homolytic Cleavage

11:59

Bond Dissociation Energy (BDE) Table

12:29

BDE for Multiple Bonds

14:32

Examples

17:35

Kinetics

20:35

Kinetics

20:36

Examples

21:49

Reaction Rate Variables

23:15

Reaction Rate Variables

23:16

Increasing Temperature, Increasing Rate

24:08

Increasing Concentration, Increasing Rate

25:39

Decreasing Energy of Activation, Increasing Rate

27:49

Two-Step Mechanisms

30:06

E vs. POR Diagram (2-step Mechanism)

30:07

Reactive Intermediates

33:03

Reactive Intermediates

33:04

Example: A Carbocation

35:20

Carbocation Stability

37:24

Relative Stability of Carbocation

37:25

Alkyl groups and Hyperconjugation

38:45

Carbocation Stability

41:57

Carbocation Stabilized by Resonance: Allylic

41:58

Carbocation Stabilized by Resonance: Benzylic

42:59

Overall Carbocation Stability

44:05

Free Radicals

45:05

Definition and Examples of Free Radicals

45:06

Radical Mechanisms

49:40

Example: Regular Arrow

49:41

Example: Fish-Hook Arrow

50:17

Free Radical Halogenation

26m 23s

Intro

0:00

Free Radical Halogenation

0:06

Free Radical Halogenation

0:07

Mechanism: Initiation

1:27

Mechanism: Propagation Steps

2:21

Free Radical Halogenation

5:33

Termination Steps

5:36

Example 1: Terminations Steps

6:00

Example 2: Terminations Steps

6:18

Example 3: Terminations Steps

7:43

Example 4: Terminations Steps

8:04

Regiochemistry of Free Radical Halogenation

9:32

Which Site/Region Reacts and Why?

9:34

Bromination and Rate of Reaction

14:03

Regiochemistry of Free Radical Halogenation

14:30

Chlorination

14:31

Why the Difference in Selectivity?

19:58

Allylic Halogenation

20:53

Examples of Allylic Halogenation

20:55

Substitution Reactions

1h 48m 5s

Intro

0:00

Substitution Reactions

0:06

Substitution Reactions Example

0:07

Nucleophile

0:39

Electrophile

1:20

Leaving Group

2:56

General Reaction

4:13

Substitution Reactions

4:43

General Reaction

4:46

Substitution Reaction Mechanisms: Simultaneous

5:08

Substitution Reaction Mechanisms: Stepwise

5:34

SN2 Substitution

6:21

Example of SN2 Mechanism

6:22

SN2 Kinetics

7:58

Rate of SN2

9:10

Sterics Affect Rate of SN2

9:12

Rate of SN2 (By Type of RX)

14:13

SN2: E vs. POR Diagram

17:26

E vs. POR Diagram

17:27

Transition State (TS)

18:24

SN2 Transition State, Kinetics

20:58

SN2 Transition State, Kinetics

20:59

Hybridization of TS Carbon

21:57

Example: Allylic LG

23:34

Stereochemistry of SN2

25:46

Backside Attack and Inversion of Stereochemistry

25:48

SN2 Summary

29:56

Summary of SN2

29:58

Predict Products (SN2)

31:42

Example 1: Predict Products

31:50

Example 2: Predict Products

33:38

Example 3: Predict Products

35:11

Example 4: Predict Products

36:11

Example 5: Predict Products

37:32

SN1 Substitution Mechanism

41:52

Is This Substitution? Could This Be an SN2 Mechanism?

41:54

SN1 Mechanism

43:50

Two Key Steps: 1. Loss of LG

43:53

Two Key Steps: 2. Addition of nu

45:11

SN1 Kinetics

47:17

Kinetics of SN1

47:18

Rate of SN1 (By RX type)

48:44

SN1 E vs. POR Diagram

49:49

E vs. POR Diagram

49:51

First Transition Stage (TS-1)

51:48

Second Transition Stage (TS-2)

52:56

Stereochemistry of SN1

53:44

Racemization of SN1 and Achiral Carbocation Intermediate

53:46

Example

54:29

SN1 Summary

58:25

Summary of SN1

58:26

SN1 or SN2 Mechanisms?

1:00:40

Example 1: SN1 or SN2 Mechanisms

1:00:42

Example 2: SN1 or SN2 Mechanisms

1:03:00

Example 3: SN1 or SN2 Mechanisms

1:04:06

Example 4: SN1 or SN2 Mechanisms

1:06:17

SN1 Mechanism

1:09:12

Three Steps of SN1 Mechanism

1:09:13

SN1 Carbocation Rearrangements

1:14:50

Carbocation Rearrangements Example

1:14:51

SN1 Carbocation Rearrangements

1:20:46

Alkyl Groups Can Also Shift

1:20:48

Leaving Groups

1:24:26

Leaving Groups

1:24:27

Forward or Reverse Reaction Favored?

1:26:00

Leaving Groups

1:29:59

Making poor LG Better: Method 1

1:30:00

Leaving Groups

1:34:18

Making poor LG Better: Tosylate (Method 2)

1:34:19

Synthesis Problem

1:38:15

Example: Provide the Necessary Reagents

1:38:16

Nucleophilicity

1:41:10

What Makes a Good Nucleophile?

1:41:11

Nucleophilicity

1:44:45

Periodic Trends: Across Row

1:44:47

Periodic Trends: Down a Family

1:46:46

Elimination Reactions

1h 11m 43s

Intro

0:00

Elimination Reactions: E2 Mechanism

0:06

E2 Mechanism

0:08

Example of E2 Mechanism

1:01

Stereochemistry of E2

4:48

Anti-Coplanar & Anti-Elimination

4:50

Example 1: Stereochemistry of E2

5:34

Example 2: Stereochemistry of E2

10:39

Regiochemistry of E2

13:04

Refiochemistry of E2 and Zaitsev's Rule

13:05

Alkene Stability

17:39

Alkene Stability

19:20

Alkene Stability Examples

19:22

Example 1: Draw Both E2 Products and Select Major

21:57

Example 2: Draw Both E2 Products and Select Major

25:02

SN2 Vs. E2 Mechanisms

29:06

SN2 Vs. E2 Mechanisms

29:07

When Do They Compete?

30:34

SN2 Vs. E2 Mechanisms

31:23

Compare Rates

31:24

SN2 Vs. E2 Mechanisms

36:34

t-BuBr: What If Vary Base?

36:35

Preference for E2 Over SN2 (By RX Type)

40:42

E1 Elimination Mechanism

41:51

E1 - Elimination Unimolecular

41:52

E1 Mechanism: Step 1

44:14

E1 Mechanism: Step 2

44:48

E1 Kinetics

46:58

Rate = k[RCI]

47:00

E1 Rate (By Type of Carbon Bearing LG)

48:31

E1 Stereochemistry

49:49

Example 1: E1 Stereochemistry

49:51

Example 2: E1 Stereochemistry

52:31

Carbocation Rearrangements

55:57

Carbocation Rearrangements

56:01

Product Mixtures

57:20

Predict the Product: SN2 vs. E2

59:58

Example 1: Predict the Product

1:00:00

Example 2: Predict the Product

1:02:10

Example 3: Predict the Product

1:04:07

Predict the Product: SN2 vs. E2

1:06:06

Example 4: Predict the Product

1:06:07

Example 5: Predict the Product

1:07:29

Example 6: Predict the Product

1:07:51

Example 7: Predict the Product

1:09:18

Section 3: Alkanes, Alkenes, & Alkynes

Alkenes

36m 39s

Intro

0:00

Alkenes

0:12

Definition and Structure of Alkenes

0:13

3D Sketch of Alkenes

1:53

Pi Bonds

3:48

Alkene Stability

4:57

Alkyl Groups Attached

4:58

Trans & Cis

6:20

Alkene Stability

8:42

Pi Bonds & Conjugation

8:43

Bridgehead Carbons & Bredt's Rule

10:22

Measuring Stability: Hydrogenation Reaction

11:40

Alkene Synthesis

12:01

Method 1: E2 on Alkyl Halides

12:02

Review: Stereochemistry

16:17

Review: Regiochemistry

16:50

Review: SN2 vs. E2

17:34

Alkene Synthesis

18:57

Method 2: Dehydration of Alcohols

18:58

Mechanism

20:08

Alkene Synthesis

23:26

Alcohol Dehydration

23:27

Example 1: Comparing Strong Acids

26:59

Example 2: Mechanism for Dehydration Reaction

29:00

Example 3: Transform

32:50

Reactions of Alkenes

2h 8m 44s

Intro

0:00

Reactions of Alkenes

0:05

Electrophilic Addition Reaction

0:06

Addition of HX

2:02

Example: Regioselectivity & 2 Steps Mechanism

2:03

Markovnikov Addition

5:30

Markovnikov Addition is Favored

5:31

Graph: E vs. POR

6:33

Example

8:29

Example: Predict and Consider the Stereochemistry

8:30

Hydration of Alkenes

12:31

Acid-catalyzed Addition of Water

12:32

Strong Acid

14:20

Hydration of Alkenes

15:20

Acid-catalyzed Addition of Water: Mechanism

15:21

Hydration vs. Dehydration

19:51

Hydration Mechanism is Exact Reverse of Dehydration

19:52

Example

21:28

Example: Hydration Reaction

21:29

Alternative 'Hydration' Methods

25:26

Oxymercuration-Demercuration

25:27

Oxymercuration Mechanism

28:55

Mechanism of Oxymercuration

28:56

Alternative 'Hydration' Methods

30:51

Hydroboration-Oxidation

30:52

Hydroboration Mechanism

33:22

1-step (concerted)

33:23

Regioselective

34:45

Stereoselective

35:30

Example

35:58

Example: Hydroboration-Oxidation

35:59

Example

40:42

Example: Predict the Major Product

40:43

Synthetic Utility of 'Alternate' Hydration Methods

44:36

Example: Synthetic Utility of 'Alternate' Hydration Methods

44:37

Flashcards

47:28

Tips On Using Flashcards

47:29

Bromination of Alkenes

49:51

Anti-Addition of Br₂

49:52

Bromination Mechanism

53:16

Mechanism of Bromination

53:17

Bromination Mechanism

55:42

Mechanism of Bromination

55:43

Bromination: Halohydrin Formation

58:54

Addition of other Nu: to Bromonium Ion

58:55

Mechanism

1:00:08

Halohydrin: Regiochemistry

1:03:55

Halohydrin: Regiochemistry

1:03:56

Bromonium Ion Intermediate

1:04:26

Example

1:09:28

Example: Predict Major Product

1:09:29

Example Cont.

1:10:59

Example: Predict Major Product Cont.

1:11:00

Catalytic Hydrogenation of Alkenes

1:13:19

Features of Catalytic Hydrogenation

1:13:20

Catalytic Hydrogenation of Alkenes

1:14:48

Metal Surface

1:14:49

Heterogeneous Catalysts

1:15:29

Homogeneous Catalysts

1:16:08

Catalytic Hydrogenation of Alkenes

1:17:44

Hydrogenation & Pi Bond Stability

1:17:45

Energy Diagram

1:19:22

Catalytic Hydrogenation of Dienes

1:20:40

Hydrogenation & Pi Bond Stability

1:20:41

Energy Diagram

1:23:31

Example

1:24:14

Example: Predict Product

1:24:15

Oxidation of Alkenes

1:27:21

Redox Review

1:27:22

Epoxide

1:30:26

Diol (Glycol)

1:30:54

Ketone/ Aldehyde

1:31:13

Epoxidation

1:32:08

Epoxidation

1:32:09

General Mechanism

1:36:32

Alternate Epoxide Synthesis

1:37:38

Alternate Epoxide Synthesis

1:37:39

Dihydroxylation

1:41:10

Dihydroxylation

1:41:12

General Mechanism (Concerted Via Cycle Intermediate)

1:42:38

Ozonolysis

1:44:22

Ozonolysis: Introduction

1:44:23

Ozonolysis: Is It Good or Bad?

1:45:05

Ozonolysis Reaction

1:48:54

Examples

1:51:10

Example 1: Ozonolysis

1:51:11

Example

1:53:25

Radical Addition to Alkenes

1:55:05

Recall: Free-Radical Halogenation

1:55:15

Radical Mechanism

1:55:45

Propagation Steps

1:58:01

Atom Abstraction

1:58:30

Addition to Alkene

1:59:11

Radical Addition to Alkenes

1:59:54

Markovnivok (Electrophilic Addition) & anti-Mark. (Radical Addition)

1:59:55

Mechanism

2:01:03

Alkene Polymerization

2:05:35

Example: Alkene Polymerization

2:05:36

Alkynes

1h 13m 19s

Intro

0:00

Structure of Alkynes

0:04

Structure of Alkynes

0:05

3D Sketch

2:30

Internal and Terminal

4:03

Reductions of Alkynes

4:36

Catalytic Hydrogenation

4:37

Lindlar Catalyst

5:25

Reductions of Alkynes

7:24

Dissolving Metal Reduction

7:25

Oxidation of Alkynes

9:24

Ozonolysis

9:25

Reactions of Alkynes

10:56

Addition Reactions: Bromination

10:57

Addition of HX

12:24

Addition of HX

12:25

Addition of HX

13:36

Addition of HX: Mechanism

13:37

Example

17:38

Example: Transform

17:39

Hydration of Alkynes

23:35

Hydration of Alkynes

23:36

Hydration of Alkynes

26:47

Hydration of Alkynes: Mechanism

26:49

'Hydration' via Hydroboration-Oxidation

32:57

'Hydration' via Hydroboration-Oxidation

32:58

Disiamylborane

33:28

Hydroboration-Oxidation Cont.

34:25

Alkyne Synthesis

36:17

Method 1: Alkyne Synthesis By Dehydrohalogenation

36:19

Alkyne Synthesis

39:06

Example: Transform

39:07

Alkyne Synthesis

41:21

Method 2 & Acidity of Alkynes

41:22

Conjugate Bases

43:06

Preparation of Acetylide Anions

49:55

Preparation of Acetylide Anions

49:57

Alkyne Synthesis

53:40

Synthesis Using Acetylide Anions

53:41

Example 1: Transform

57:04

Example 2: Transform

1:01:07

Example 3: Transform

1:06:22

Section 4: Alcohols

Alcohols, Part I

59m 52s

Intro

0:00

Alcohols

0:11

Attributes of Alcohols

0:12

Boiling Points

2:00

Water Solubility

5:00

Water Solubility (Like Dissolves Like)

5:01

Acidity of Alcohols

9:39

Comparison of Alcohols Acidity

9:41

Preparation of Alkoxides

13:03

Using Strong Base Like Sodium Hydride

13:04

Using Redox Reaction

15:36

Preparation of Alkoxides

17:41

Using K°

17:42

Phenols Are More Acidic Than Other Alcohols

19:51

Synthesis of Alcohols, ROH

21:43

Synthesis of Alcohols from Alkyl Halides, RX (SN2 or SN1)

21:44

Synthesis of Alcohols, ROH

25:08

Unlikely on 2° RX (E2 Favored)

25:09

Impossible on 3° RX (E2) and Phenyl/Vinyl RX (N/R)

25:47

Synthesis of Alcohols, ROH

26:26

SN1 with H₂O 'Solvolysis' or 'Hydrolysis'

26:27

Carbocation Can Rearrange

29:00

Synthesis of Alcohols, ROH

30:08

Synthesis of Alcohols From Alkenes: Hydration

30:09

Synthesis of Alcohols From Alkenes: Oxidation/Diol

32:20

Synthesis of Alcohols, ROH

33:14

Synthesis of Alcohols From Ketones and Aldehydes

33:15

Organometallic Reagents: Preparation

37:03

Grignard (RMgX)

37:04

Organolithium (Rli)

40:03

Organometallic Reagents: Reactions

41:45

Reactions of Organometallic Reagents

41:46

Organometallic Reagents: Reactions as Strong Nu:

46:40

Example 1: Reactions as Strong Nu:

46:41

Example 2: Reactions as Strong Nu:

48:57

Hydride Nu:

50:52

Hydride Nu:

50:53

Examples

53:34

Predict 1

53:35

Predict 2

54:45

Examples

56:43

Transform

56:44

Provide Starting Material

58:18

Alcohols, Part II

45m 35s

Intro

0:00

Oxidation Reactions

0:08

Oxidizing Agents: Jones, PCC, Swern

0:09

'Jones' Oxidation

0:43

Example 1: Predict Oxidation Reactions

2:29

Example 2: Predict Oxidation Reactions

3:00

Oxidation Reactions

4:11

Selective Oxidizing Agents (PCC and Swern)

4:12

PCC (Pyridiniym Chlorochromate)

5:10

Swern Oxidation

6:05

General [ox] Mechanism

8:32

General [ox] Mechanism

8:33

Oxidation of Alcohols

10:11

Example 1: Oxidation of Alcohols

10:12

Example 2: Oxidation of Alcohols

11:20

Example 3: Oxidation of Alcohols

11:46

Example

13:09

Predict: PCC Oxidation Reactions

13:10

Tosylation of Alcohols

15:22

Introduction to Tosylation of Alcohols

15:23

Example

21:08

Example: Tosylation of Alcohols

21:09

Reductions of Alcohols

23:39

Reductions of Alcohols via SN2 with Hydride

24:22

Reductions of Alcohols via Dehydration

27:12

Conversion of Alcohols to Alkyl Halides

30:12

Conversion of Alcohols to Alkyl Halides via Tosylate

30:13

Conversion of Alcohols to Alkyl Halides

31:17

Using HX

31:18

Mechanism

32:09

Conversion of Alcohols to Alkyl Halides

35:43

Reagents that Provide LG and Nu: in One 'Pot'

35:44

General Mechanisms

37:44

Example 1: General Mechanisms

37:45

Example 2: General Mechanisms

39:25

Example

41:04

Transformation of Alcohols

41:05

Section 5: Ethers, Thiols, Thioethers, & Ketones

Ethers

1h 34m 45s

Intro

0:00

Ethers

0:11

Overview of Ethers

0:12

Boiling Points

1:37

Ethers

4:34

Water Solubility (Grams per 100mL H₂O)

4:35

Synthesis of Ethers

7:53

Williamson Ether Synthesis

7:54

Example: Synthesis of Ethers

9:23

Synthesis of Ethers

10:27

Example: Synthesis of Ethers

10:28

Intramolecular SN2

13:04

Planning an Ether Synthesis

14:45

Example 1: Planning an Ether Synthesis

14:46

Planning an Ether Synthesis

16:16

Example 2: Planning an Ether Synthesis

16:17

Planning an Ether Synthesis

22:04

Example 3: Synthesize Dipropyl Ether

22:05

Planning an Ether Synthesis

26:01

Example 4: Transform

26:02

Synthesis of Epoxides

30:05

Synthesis of Epoxides Via Williamson Ether Synthesis

30:06

Synthesis of Epoxides Via Oxidation

32:42

Reaction of Ethers

33:35

Reaction of Ethers

33:36

Reactions of Ethers with HBr or HI

34:44

Reactions of Ethers with HBr or HI

34:45

Mechanism

35:25

Epoxide Ring-Opening Reaction

39:25

Epoxide Ring-Opening Reaction

39:26

Example: Epoxide Ring-Opening Reaction

42:42

Acid-Catalyzed Epoxide Ring Opening

44:16

Acid-Catalyzed Epoxide Ring Opening Mechanism

44:17

Acid-Catalyzed Epoxide Ring Opening

50:13

Acid-Catalyzed Epoxide Ring Opening Mechanism

50:14

Catalyst Needed for Ring Opening

53:34

Catalyst Needed for Ring Opening

53:35

Stereochemistry of Epoxide Ring Opening

55:56

Stereochemistry: SN2 Mechanism

55:57

Acid or Base Mechanism?

58:30

Example

1:01:03

Transformation

1:01:04

Regiochemistry of Epoxide Ring Openings

1:05:29

Regiochemistry of Epoxide Ring Openings in Base

1:05:30

Regiochemistry of Epoxide Ring Openings in Acid

1:07:34

Example

1:10:26

Example 1: Epoxide Ring Openings in Base

1:10:27

Example 2: Epoxide Ring Openings in Acid

1:12:50

Reactions of Epoxides with Grignard and Hydride

1:15:35

Reactions of Epoxides with Grignard and Hydride

1:15:36

Example

1:21:47

Example: Ethers

1:21:50

Example

1:27:01

Example: Synthesize

1:27:02

Thiols and Thioethers

16m 50s

Intro

0:00

Thiols and Thioethers

0:10

Physical Properties

0:11

Reactions Can Be Oxidized

2:16

Acidity of Thiols

3:11

Thiols Are More Acidic Than Alcohols

3:12

Synthesis of Thioethers

6:44

Synthesis of Thioethers

6:45

Example

8:43

Example: Synthesize the Following Target Molecule

8:44

Example

14:18

Example: Predict

14:19

Ketones

2h 18m 12s

Intro

0:00

Aldehydes & Ketones

0:11

The Carbonyl: Resonance & Inductive

0:12

Reactivity

0:50

The Carbonyl

2:35

The Carbonyl

2:36

Carbonyl FG's

4:10

Preparation/Synthesis of Aldehydes & Ketones

6:18

Oxidation of Alcohols

6:19

Ozonolysis of Alkenes

7:16

Hydration of Alkynes

8:01

Reaction with Hydride Nu:

9:00

Reaction with Hydride Nu:

9:01

Reaction with Carbon Nu:

11:29

Carbanions: Acetylide

11:30

Carbanions: Cyanide

14:23

Reaction with Carbon Nu:

15:32

Organometallic Reagents (RMgX, Rli)

15:33

Retrosynthesis of Alcohols

17:04

Retrosynthesis of Alcohols

17:05

Example

19:30

Example: Transform

19:31

Example

22:57

Example: Transform

22:58

Example

28:19

Example: Transform

28:20

Example

33:36

Example: Transform

33:37

Wittig Reaction

37:39

Wittig Reaction: A Resonance-Stabilized Carbanion (Nu:)

37:40

Wittig Reaction: Mechanism

39:51

Preparation of Wittig Reagent

41:58

Two Steps From RX

41:59

Example: Predict

45:02

Wittig Retrosynthesis

46:19

Wittig Retrosynthesis

46:20

Synthesis

48:09

Reaction with Oxygen Nu:

51:21

Addition of H₂O

51:22

Exception: Formaldehyde is 99% Hydrate in H₂O Solution

54:10

Exception: Hydrate is Favored if Partial Positive Near Carbonyl

55:26

Reaction with Oxygen Nu:

57:45

Addition of ROH

57:46

TsOH: Tosic Acid

58:28

Addition of ROH Cont.

59:09

Example

1:01:43

Predict

1:01:44

Mechanism

1:03:08

Mechanism for Acetal Formation

1:04:10

Mechanism for Acetal Formation

1:04:11

What is a CTI?

1:15:04

Tetrahedral Intermediate

1:15:05

Charged Tetrahedral Intermediate

1:15:45

CTI: Acid-cat

1:16:10

CTI: Base-cat

1:17:01

Acetals & Cyclic Acetals

1:17:49

Overall

1:17:50

Cyclic Acetals

1:18:46

Hydrolysis of Acetals: Regenerates Carbonyl

1:20:01

Hydrolysis of Acetals: Regenerates Carbonyl

1:20:02

Mechanism

1:22:08

Reaction with Nitrogen Nu:

1:30:11

Reaction with Nitrogen Nu:

1:30:12

Example

1:32:18

Mechanism of Imine Formation

1:33:24

Mechanism of Imine Formation

1:33:25

Oxidation of Aldehydes

1:38:12

Oxidation of Aldehydes 1

1:38:13

Oxidation of Aldehydes 2

1:39:52

Oxidation of Aldehydes 3

1:40:10

Reductions of Ketones and Aldehydes

1:40:54

Reductions of Ketones and Aldehydes

1:40:55

Hydride/ Workup

1:41:22

Raney Nickel

1:42:07

Reductions of Ketones and Aldehydes

1:43:24

Clemmensen Reduction & Wolff-Kishner Reduction

1:43:40

Acetals as Protective Groups

1:46:50

Acetals as Protective Groups

1:46:51

Example

1:50:39

Example: Consider the Following Synthesis

1:50:40

Protective Groups

1:54:47

Protective Groups

1:54:48

Example

1:59:02

Example: Transform

1:59:03

Example: Another Route

2:04:54

Example: Transform

2:08:49

Example

2:08:50

Transform

2:08:51

Example

2:11:05

Transform

2:11:06

Example

2:13:45

Transform

2:13:46

Example

2:15:43

Provide the Missing Starting Material

2:15:44

Section 6: Organic Transformation Practice

Transformation Practice Problems

38m 58s

Intro

0:00

Practice Problems

0:33

Practice Problem 1: Transform

0:34

Practice Problem 2: Transform

3:57

Practice Problems

7:49

Practice Problem 3: Transform

7:50

Practice Problems

15:32

Practice Problem 4: Transform

15:34

Practice Problem 5: Transform

20:15

Practice Problems

24:08

Practice Problem 6: Transform

24:09

Practice Problem 7: Transform

29:27

Practice Problems

33:08

Practice Problem 8: Transform

33:09

Practice Problem 9: Transform

35:23

Section 7: Carboxylic Acids

Carboxylic Acids

1h 17m 51s

Intro

0:00

Review Reactions of Ketone/Aldehyde

0:06

Carbonyl Reactivity

0:07

Nu: = Hydride (Reduction)

1:37

Nu: = Grignard

2:08

Review Reactions of Ketone/Aldehyde

2:53

Nu: = Alcohol

2:54

Nu: = Amine

3:46

Carboxylic Acids and Their Derivatives

4:37

Carboxylic Acids and Their Derivatives

4:38

Ketone vs. Ester Reactivity

6:33

Ketone Reactivity

6:34

Ester Reactivity

6:55

Carboxylic Acids and Their Derivatives

7:30

Acid Halide, Anhydride, Ester, Amide, and Nitrile

7:43

General Reactions of Acarboxylic Acid Derivatives

9:22

General Reactions of Acarboxylic Acid Derivatives

9:23

Physical Properties of Carboxylic Acids

12:16

Acetic Acid

12:17

Carboxylic Acids

15:46

Aciditiy of Carboxylic Acids, RCO₂H

17:45

Alcohol

17:46

Carboxylic Acid

19:21

Aciditiy of Carboxylic Acids, RCO₂H

21:31

Aciditiy of Carboxylic Acids, RCO₂H

21:32

Aciditiy of Carboxylic Acids, RCO₂H

24:48

Example: Which is the Stronger Acid?

24:49

Aciditiy of Carboxylic Acids, RCO₂H

30:06

Inductive Effects Decrease with Distance

30:07

Preparation of Carboxylic Acids, RCO₂H

31:55

A) By Oxidation

31:56

Preparation of Carboxylic Acids, RCO₂H

34:37

Oxidation of Alkenes/Alkynes - Ozonolysis

34:38

Preparation of Carboxylic Acids, RCO₂H

36:17

B) Preparation of RCO₂H from Organometallic Reagents

36:18

Preparation of Carboxylic Acids, RCO₂H

38:02

Example: Preparation of Carboxylic Acids

38:03

Preparation of Carboxylic Acids, RCO₂H

40:38

C) Preparation of RCO₂H by Hydrolysis of Carboxylic Acid Derivatives

40:39

Hydrolysis Mechanism

42:19

Hydrolysis Mechanism

42:20

Mechanism: Acyl Substitution (Addition/Elimination)

43:05

Hydrolysis Mechanism

47:27

Substitution Reaction

47:28

RO is Bad LG for SN1/SN2

47:39

RO is okay LG for Collapse of CTI

48:31

Hydrolysis Mechanism

50:07

Base-promoted Ester Hydrolysis (Saponification)

50:08

Applications of Carboxylic Acid Derivatives:

53:10

Saponification Reaction

53:11

Ester Hydrolysis

57:15

Acid-Catalyzed Mechanism

57:16

Ester Hydrolysis Requires Acide or Base

1:03:06

Ester Hydrolysis Requires Acide or Base

1:03:07

Nitrile Hydrolysis

1:05:22

Nitrile Hydrolysis

1:05:23

Nitrile Hydrolysis Mechanism

1:06:53

Nitrile Hydrolysis Mechanism

1:06:54

Use of Nitriles in Synthesis

1:12:39

Example: Nitirles in Synthesis

1:12:40

Carboxylic Acid Derivatives

1h 21m 4s

Intro

0:00

Carboxylic Acid Derivatives

0:05

Carboxylic Acid Derivatives

0:06

General Structure

1:00

Preparation of Carboxylic Acid Derivatives

1:19

Which Carbonyl is the Better E+?

1:20

Inductive Effects

1:54

Resonance

3:23

Preparation of Carboxylic Acid Derivatives

6:52

Which is Better E+, Ester or Acid Chloride?

6:53

Inductive Effects

7:02

Resonance

7:20

Preparation of Carboxylic Acid Derivatives

10:45

Which is Better E+, Carboxylic Acid or Anhydride?

10:46

Inductive Effects & Resonance

11:00

Overall: Order of Electrophilicity and Leaving Group

14:49

Order of Electrophilicity and Leaving Group

14:50

Example: Acid Chloride

16:26

Example: Carboxylate

19:17

Carboxylic Acid Derivative Interconversion

20:53

Carboxylic Acid Derivative Interconversion

20:54

Preparation of Acid Halides

24:31

Preparation of Acid Halides

24:32

Preparation of Anhydrides

25:45

A) Dehydration of Acids (For Symmetrical Anhydride)

25:46

Preparation of Anhydrides

27:29

Example: Dehydration of Acids

27:30

Preparation of Anhydrides

29:16

B) From an Acid Chloride (To Make Mixed Anhydride)

29:17

Mechanism

30:03

Preparation of Esters

31:53

A) From Acid Chloride or Anhydride

31:54

Preparation of Esters

33:48

B) From Carboxylic Acids (Fischer Esterification)

33:49

Mechanism

36:55

Preparations of Esters

41:38

Example: Predict the Product

41:39

Preparation of Esters

43:17

C) Transesterification

43:18

Mechanism

45:17

Preparation of Esters

47:58

D) SN2 with Carboxylate

47:59

Mechanism: Diazomethane

49:28

Preparation of Esters

51:01

Example: Transform

51:02

Preparation of Amides

52:27

A) From an Acid Cl or Anhydride

52:28

Preparations of Amides

54:47

B) Partial Hydrolysis of Nitriles

54:48

Preparation of Amides

56:11

Preparation of Amides: Find Alternate Path

56:12

Preparation of Amides

59:04

C) Can't be Easily Prepared from RCO₂H Directly

59:05

Reactions of Carboxylic Acid Derivatives with Nucleophiles

1:01:41

A) Hydride Nu: Review

1:01:42

A) Hydride Nu: Sodium Borohydride + Ester

1:02:43

Reactions of Carboxylic Acid Derivatives with Nucleophiles

1:03:57

Lithium Aluminum Hydride (LAH)

1:03:58

Mechanism

1:04:29

Summary of Hydride Reductions

1:07:09

Summary of Hydride Reductions 1

1:07:10

Summary of Hydride Reductions 2

1:07:36

Hydride Reduction of Amides

1:08:12

Hydride Reduction of Amides Mechanism

1:08:13

Reaction of Carboxylic Acid Derivatives with Organometallics

1:12:04

Review 1

1:12:05

Review 2

1:12:50

Reaction of Carboxylic Acid Derivatives with Organometallics

1:14:22

Example: Lactone

1:14:23

Special Hydride Nu: Reagents

1:16:34

Diisobutylaluminum Hydride

1:16:35

Example

1:17:25

Other Special Hydride

1:18:41

Addition of Organocuprates to Acid Chlorides

1:19:07

Addition of Organocuprates to Acid Chlorides

1:19:08

Section 8: Enols & Enolates

Enols and Enolates, Part 1

1h 26m 22s

Intro

0:00

Enols and Enolates

0:09

The Carbonyl

0:10

Keto-Enol Tautomerization

1:17

Keto-Enol Tautomerization Mechanism

2:28

Tautomerization Mechanism (2 Steps)

2:29

Keto-Enol Tautomerization Mechanism

5:15

Reverse Reaction

5:16

Mechanism

6:07

Formation of Enolates

7:27

Why is a Ketone's α H's Acidic?

7:28

Formation of Other Carbanions

10:05

Alkyne

10:06

Alkane and Alkene

10:53

Formation of an Enolate: Choice of Base

11:27

Example: Choice of Base

11:28

Formation of an Enolate: Choice of Base

13:56

Deprotonate, Stronger Base, and Lithium Diisopropyl Amide (LDA)

13:57

Formation of an Enolate: Choice of Base

15:48

Weaker Base & 'Active' Methylenes

15:49

Why Use NaOEt instead of NaOH?

19:01

Other Acidic 'α' Protons

20:30

Other Acidic 'α' Protons

20:31

Why is an Ester Less Acidic than a Ketone?

24:10

Other Acidic 'α' Protons

25:19

Other Acidic 'α' Protons Continue

25:20

How are Enolates Used

25:54

Enolates

25:55

Possible Electrophiles

26:21

Alkylation of Enolates

27:56

Alkylation of Enolates

27:57

Resonance Form

30:03

α-Halogenation

32:17

α-Halogenation

32:18

Iodoform Test for Methyl Ketones

33:47

α-Halogenation

35:55

Acid-Catalyzed

35:57

Mechanism: 1st Make Enol (2 Steps)

36:14

Whate Other Eloctrophiles ?

39:17

Aldol Condensation

39:38

Aldol Condensation

39:39

Aldol Mechanism

41:26

Aldol Mechanism: In Base, Deprotonate First

41:27

Aldol Mechanism

45:28

Mechanism for Loss of H₂O

45:29

Collapse of CTI and β-elimination Mechanism

47:51

Loss of H₂0 is not E2!

48:39

Aldol Summary

49:53

Aldol Summary

49:54

Base-Catalyzed Mechanism

52:34

Acid-Catalyzed Mechansim

53:01

Acid-Catalyzed Aldol Mechanism

54:01

First Step: Make Enol

54:02

Acid-Catalyzed Aldol Mechanism

56:54

Loss of H₂0 (β elimination)

56:55

Crossed/Mixed Aldol

1:00:55

Crossed/Mixed Aldol & Compound with α H's

1:00:56

Ketone vs. Aldehyde

1:02:30

Crossed/Mixed Aldol & Compound with α H's Continue

1:03:10

Crossed/Mixed Aldol

1:05:21

Mixed Aldol: control Using LDA

1:05:22

Crossed/Mixed Aldol Retrosynthesis

1:08:53

Example: Predic Aldol Starting Material (Aldol Retrosyntheiss)

1:08:54

Claisen Condensation

1:12:54

Claisen Condensation (Aldol on Esters)

1:12:55

Claisen Condensation

1:19:52

Example 1: Claisen Condensation

1:19:53

Claisen Condensation

1:22:48

Example 2: Claisen Condensation

1:22:49

Enols and Enolates, Part 2

50m 57s

Intro

0:00

Conjugate Additions

0:06

α, β-unsaturated Carbonyls

0:07

Conjugate Additions

1:50

'1,2-addition'

1:51

'1,-4-addition' or 'Conjugate Addition'

2:24

Conjugate Additions

4:53

Why can a Nu: Add to this Alkene?

4:54

Typical Alkene

5:09

α, β-unsaturated Alkene

5:39

Electrophilic Alkenes: Michael Acceptors

6:35

Other 'Electrophilic' Alkenes (Called 'Michael Acceptors)

6:36

1,4-Addition of Cuprates (R2CuLi)

8:29

1,4-Addition of Cuprates (R2CuLi)

8:30

1,4-Addition of Cuprates (R2CuLi)

11:23

Use Cuprates in Synthesis

11:24

Preparation of Cuprates

12:25

Prepare Organocuprate From Organolithium

12:26

Cuprates Also Do SN2 with RX E+ (Not True for RMgX, RLi)

13:06

1,4-Addition of Enolates: Michael Reaction

13:50

1,4-Addition of Enolates: Michael Reaction

13:51

Mechanism

15:57

1,4-Addition of Enolates: Michael Reaction

18:47

Example: 1,4-Addition of Enolates

18:48

1,4-Addition of Enolates: Michael Reaction

21:02

Michael Reaction, Followed by Intramolecular Aldol

21:03

Mechanism of the Robinson Annulation

24:26

Mechanism of the Robinson Annulation

24:27

Enols and Enolates: Advanced Synthesis Topics

31:10

Stablized Enolates and the Decarboxylation Reaction

31:11

Mechanism: A Pericyclic Reaction

32:08

Enols and Enolates: Advanced Synthesis Topics

33:32

Example: Advance Synthesis

33:33

Enols and Enolates: Advanced Synthesis Topics

36:10

Common Reagents: Diethyl Malonate

36:11

Common Reagents: Ethyl Acetoacetate

37:27

Enols and Enolates: Advanced Synthesis Topics

38:06

Example: Transform

38:07

Advanced Synthesis Topics: Enamines

41:52

Enamines

41:53

Advanced Synthesis Topics: Enamines

43:06

Reaction with Ketone/Aldehyde

43:07

Example

44:08

Advanced Synthesis Topics: Enamines

45:31

Example: Use Enamines as Nu: (Like Enolate)

45:32

Advanced Synthesis Topics: Enamines

47:56

Example

47:58

Section 9: Aromatic Compounds

Aromatic Compounds: Structure

1h 59s

Intro

0:00

Aromatic Compounds

0:05

Benzene

0:06

3D Sketch

1:33

Features of Benzene

4:41

Features of Benzene

4:42

Aromatic Stability

6:41

Resonance Stabilization of Benzene

6:42

Cyclohexatriene

7:24

Benzene (Actual, Experimental)

8:11

Aromatic Stability

9:03

Energy Graph

9:04

Aromaticity Requirements

9:55

1) Cyclic and Planar

9:56

2) Contiguous p Orbitals

10:49

3) Satisfy Huckel's Rule

11:20

Example: Benzene

12:32

Common Aromatic Compounds

13:28

Example: Pyridine

13:29

Common Aromatic Compounds

16:25

Example: Furan

16:26

Common Aromatic Compounds

19:42

Example: Thiophene

19:43

Example: Pyrrole

20:18

Common Aromatic Compounds

21:09

Cyclopentadienyl Anion

21:10

Cycloheptatrienyl Cation

23:48

Naphthalene

26:04

Determining Aromaticity

27:28

Example: Which of the Following are Aromatic?

27:29

Molecular Orbital (MO) Theory

32:26

What's So Special About '4n + 2' Electrons?

32:27

π bond & Overlapping p Orbitals

32:53

Molecular Orbital (MO) Diagrams

36:56

MO Diagram: Benzene

36:58

Drawing MO Diagrams

44:26

Example: 3-Membered Ring

44:27

Example: 4-Membered Ring

46:04

Drawing MO Diagrams

47:51

Example: 5-Membered Ring

47:52

Example: 8-Membered Ring

49:32

Aromaticity and Reactivity

51:03

Example: Which is More Acidic?

51:04

Aromaticity and Reactivity

56:03

Example: Which has More Basic Nitrogen, Pyrrole or Pyridine?

56:04

Aromatic Compounds: Reactions, Part 1

1h 24m 4s

Intro

0:00

Reactions of Benzene

0:07

N/R as Alkenes

0:08

Substitution Reactions

0:50

Electrophilic Aromatic Substitution

1:24

Electrophilic Aromatic Substitution

1:25

Mechanism Step 1: Addition of Electrophile

2:08

Mechanism Step 2: Loss of H+

4:14

Electrophilic Aromatic Substitution on Substituted Benzenes

5:21

Electron Donating Group

5:22

Electron Withdrawing Group

8:02

Halogen

9:23

Effects of Electron-Donating Groups (EDG)

10:23

Effects of Electron-Donating Groups (EDG)

10:24

What Effect Does EDG (OH) Have?

11:40

Reactivity

13:03

Regioselectivity

14:07

Regioselectivity: EDG is o/p Director

14:57

Prove It! Add E+ and Look at Possible Intermediates

14:58

Is OH Good or Bad?

17:38

Effects of Electron-Withdrawing Groups (EWG)

20:20

What Effect Does EWG Have?

20:21

Reactivity

21:28

Regioselectivity

22:24

Regioselectivity: EWG is a Meta Director

23:23

Prove It! Add E+ and Look at Competing Intermediates

23:24

Carbocation: Good or Bad?

26:01

Effects of Halogens on EAS

28:33

Inductive Withdrawal of e- Density vs. Resonance Donation

28:34

Summary of Substituent Effects on EAS

32:33

Electron Donating Group

32:34

Electron Withdrawing Group

33:37

Directing Power of Substituents

34:35

Directing Power of Substituents

34:36

Example

36:41

Electrophiles for Electrophilic Aromatic Substitution

38:43

Reaction: Halogenation

38:44

Electrophiles for Electrophilic Aromatic Substitution

40:27

Reaction: Nitration

40:28

Electrophiles for Electrophilic Aromatic Substitution

41:45

Reaction: Sulfonation

41:46

Electrophiles for Electrophilic Aromatic Substitution

43:19

Reaction: Friedel-Crafts Alkylation

43:20

Electrophiles for Electrophilic Aromatic Substitution

45:43

Reaction: Friedel-Crafts Acylation

45:44

Electrophilic Aromatic Substitution: Nitration

46:52

Electrophilic Aromatic Substitution: Nitration

46:53

Mechanism

48:56

Nitration of Aniline

52:40

Nitration of Aniline Part 1

52:41

Nitration of Aniline Part 2: Why?

54:12

Nitration of Aniline

56:10

Workaround: Protect Amino Group as an Amide

56:11

Electrophilic Aromatic Substitution: Sulfonation

58:16

Electrophilic Aromatic Substitution: Sulfonation

58:17

Example: Transform

59:25

Electrophilic Aromatic Substitution: Friedel-Crafts Alkylation

1:02:24

Electrophilic Aromatic Substitution: Friedel-Crafts Alkylation

1:02:25

Example & Mechanism

1:03:37

Friedel-Crafts Alkylation Drawbacks

1:05:48

A) Can Over-React (Dialkylation)

1:05:49

Friedel-Crafts Alkylation Drawbacks

1:08:21

B) Carbocation Can Rearrange

1:08:22

Mechanism

1:09:33

Friedel-Crafts Alkylation Drawbacks

1:13:35

Want n-Propyl? Use Friedel-Crafts Acylation

1:13:36

Reducing Agents

1:16:45

Synthesis with Electrophilic Aromatic Substitution

1:18:45

Example: Transform

1:18:46

Synthesis with Electrophilic Aromatic Substitution

1:20:59

Example: Transform

1:21:00

Aromatic Compounds: Reactions, Part 2

59m 10s

Intro

0:00

Reagents for Electrophilic Aromatic Substitution

0:07

Reagents for Electrophilic Aromatic Substitution

0:08

Preparation of Diazonium Salt

2:12

Preparation of Diazonium Salt

2:13

Reagents for Sandmeyer Reactions

4:14

Reagents for Sandmeyer Reactions

4:15

Apply Diazonium Salt in Synthesis

6:20

Example: Transform

6:21

Apply Diazonium Salt in Synthesis

9:14

Example: Synthesize Following Target Molecule from Benzene or Toluene

9:15

Apply Diazonium Salt in Synthesis

14:56

Example: Transform

14:57

Reactions of Aromatic Substituents

21:56

A) Reduction Reactions

21:57

Reactions of Aromatic Substituents

23:24

B) Oxidations of Arenes

23:25

Benzylic [ox] Even Breaks C-C Bonds!

25:05

Benzylic Carbon Can't Be Quaternary

25:55

Reactions of Aromatic Substituents

26:21

Example

26:22

Review of Benzoic Acid Synthesis

27:34

Via Hydrolysis

27:35

Via Grignard

28:20

Reactions of Aromatic Substituents

29:15

C) Benzylic Halogenation

29:16

Radical Stabilities

31:55

N-bromosuccinimide (NBS)

32:23

Reactions of Aromatic Substituents

33:08

D) Benzylic Substitutions

33:09

Reactions of Aromatic Side Chains

37:08

Example: Transform

37:09

Nucleophilic Aromatic Substitution

43:13

Nucleophilic Aromatic Substitution

43:14

Nucleophilic Aromatic Substitution

47:08

Example

47:09

Mechanism

48:00

Nucleophilic Aromatic Substitution

50:43

Example

50:44

Nucleophilic Substitution: Benzyne Mechanism

52:46

Nucleophilic Substitution: Benzyne Mechanism

52:47

Nucleophilic Substitution: Benzyne Mechanism

57:31

Example: Predict Product

57:32

Section 10: Dienes & Amines

Conjugated Dienes

1h 9m 12s

Intro

0:00

Conjugated Dienes

0:08

Conjugated π Bonds

0:09

Diene Stability

2:00

Diene Stability: Cumulated

2:01

Diene Stability: Isolated

2:37

Diene Stability: Conjugated

2:51

Heat of Hydrogenation

3:00

Allylic Carbocations and Radicals

5:15

Allylic Carbocations and Radicals

5:16

Electrophilic Additions to Dienes

7:00

Alkenes

7:01

Unsaturated Ketone

7:47

Electrophilic Additions to Dienes

8:28

Conjugated Dienes

8:29

Electrophilic Additions to Dienes

9:46

Mechanism (2-Steps): Alkene

9:47

Electrophilic Additions to Dienes

11:40

Mechanism (2-Steps): Diene

11:41

1,2 'Kinetic' Product

13:08

1,4 'Thermodynamic' Product

14:47

E vs. POR Diagram

15:50

E vs. POR Diagram

15:51

Kinetic vs. Thermodynamic Control

21:56

Kinetic vs. Thermodynamic Control

21:57

How? Reaction is Reversible!

23:51

1,2 (Less Stable product)

23:52

1,4 (More Stable Product)

25:16

Diels Alder Reaction

26:34

Diels Alder Reaction

26:35

Dienophiles (E+)

29:23

Dienophiles (E+)

29:24

Alkyne Diels-Alder Example

30:48

Example: Alkyne Diels-Alder

30:49

Diels-Alder Reaction: Dienes (Nu:)

32:22

Diels-Alder ReactionL Dienes (Nu:)

32:23

Diels-Alder Reaction: Dienes

33:51

Dienes Must Have 's-cis' Conformation

33:52

Example

35:25

Diels-Alder Reaction with Cyclic Dienes

36:08

Cyclic Dienes are Great for Diels-Alder Reaction

36:09

Cyclopentadiene

37:10

Diels-Alder Reaction: Bicyclic Products

40:50

Endo vs. Exo Terminology: Norbornane & Bicyclo Heptane

40:51

Example: Bicyclo Heptane

42:29

Diels-Alder Reaction with Cyclic Dienes

44:15

Example

44:16

Stereochemistry of the Diels-Alder Reaction

47:39

Stereochemistry of the Diels-Alder Reaction

47:40

Example

48:08

Stereochemistry of the Diels-Alder Reaction

50:21

Example

50:22

Regiochemistry of the Diels-Alder Reaction

52:42

Rule: 1,2-Product Preferred Over 1,3-Product

52:43

Regiochemistry of the Diels-Alder Reaction

54:18

Rule: 1,4-Product Preferred Over 1,3-Product

54:19

Regiochemistry of the Diels-Alder Reaction

55:02

Why 1,2-Product or 1,4-Product Favored?

55:03

Example

56:11

Diels-Alder Reaction

58:06

Example: Predict

58:07

Diels-Alder Reaction

1:01:27

Explain Why No Diels-Alder Reaction Takes Place in This Case

1:01:28

Diels-Alder Reaction

1:03:09

Example: Predict

1:03:10

Diels-Alder Reaction: Synthesis Problem

1:05:39

Diels-Alder Reaction: Synthesis Problem

1:05:40

Pericyclic Reactions and Molecular Orbital (MO) Theory

1h 21m 31s

Intro

0:00

Pericyclic Reactions

0:05

Pericyclic Reactions

0:06

Electrocyclic Reactions

1:19

Electrocyclic Reactions

1:20

Electrocyclic Reactions

3:13

Stereoselectivity

3:14

Electrocyclic Reactions

8:10

Example: Predict

8:11

Sigmatropic Rearrangements

12:29

Sigmatropic Rearrangements

12:30

Cope Rearrangement

14:44

Sigmatropic Rearrangements

16:44

Claisen Rearrangement 1

16:45

Claisen Rearrangement 2

17:46

Cycloaddition Reactions

19:22

Diels-Alder

19:23

1,3-Dipolar Cycloaddition

20:32

Cycloaddition Reactions: Stereochemistry

21:58

Cycloaddition Reactions: Stereochemistry

21:59

Cycloaddition Reactions: Heat or Light?

26:00

4+2 Cycloadditions

26:01

2+2 Cycloadditions

27:23

Molecular Orbital (MO) Theory of Chemical Reactions

29:26

Example 1: Molecular Orbital Theory of Bonding

29:27

Molecular Orbital (MO) Theory of Chemical Reactions

31:59

Example 2: Molecular Orbital Theory of Bonding

32:00

Molecular Orbital (MO) Theory of Chemical Reactions

33:33

MO Theory of Aromaticity, Huckel's Rule

33:34

Molecular Orbital (MO) Theory of Chemical Reactions

36:43

Review: Molecular Orbital Theory of Conjugated Systems

36:44

Molecular Orbital (MO) Theory of Chemical Reactions

44:56

Review: Molecular Orbital Theory of Conjugated Systems

44:57

Molecular Orbital (MO) Theory of Chemical Reactions

46:54

Review: Molecular Orbital Theory of Conjugated Systems

46:55

Molecular Orbital (MO) Theory of Chemical Reactions

48:36

Frontier Molecular Orbitals are Involved in Reactions

48:37

Examples

50:20

MO Theory of Pericyclic Reactions: The Woodward-Hoffmann Rules

51:51

Heat-promoted Pericyclic Reactions and Light-promoted Pericyclic Reactions

51:52

MO Theory of Pericyclic Reactions: The Woodward-Hoffmann Rules

53:42

Why is a [4+2] Cycloaddition Thermally Allowed While the [2+2] is Not?

53:43

MO Theory of Pericyclic Reactions: The Woodward-Hoffmann Rules

56:51

Why is a [2+2] Cycloaddition Photochemically Allowed?

56:52

Pericyclic Reaction Example I

59:16

Pericyclic Reaction Example I

59:17

Pericyclic Reaction Example II

1:07:40

Pericyclic Reaction Example II

1:07:41

Pericyclic Reaction Example III: Vitamin D - The Sunshine Vitamin

1:14:22

Pericyclic Reaction Example III: Vitamin D - The Sunshine Vitamin

1:14:23

Amines

34m 58s

Intro

0:00

Amines: Properties and Reactivity

0:04

Compare Amines to Alcohols

0:05

Amines: Lower Boiling Point than ROH

0:55

1) RNH₂ Has Lower Boiling Point than ROH

0:56

Amines: Better Nu: Than ROH

2:22

2) RNH₂ is a Better Nucleophile than ROH Example 1

2:23

RNH₂ is a Better Nucleophile than ROH Example 2

3:08

Amines: Better Nu: than ROH

3:47

Example

3:48

Amines are Good Bases

5:41

3) RNH₂ is a Good Base

5:42

Amines are Good Bases

7:06

Example 1

7:07

Example 2: Amino Acid

8:27

Alkyl vs. Aryl Amines

9:56

Example: Which is Strongest Base?

9:57

Alkyl vs. Aryl Amines

14:55

Verify by Comparing Conjugate Acids

14:56

Reaction of Amines

17:42

Reaction with Ketone/Aldehyde: 1° Amine (RNH₂)

17:43

Reaction of Amines

18:48

Reaction with Ketone/Aldehyde: 2° Amine (R2NH)

18:49

Use of Enamine: Synthetic Equivalent of Enolate

20:08

Use of Enamine: Synthetic Equivalent of Enolate

20:09

Reaction of Amines

24:10

Hofmann Elimination

24:11

Hofmann Elimination

26:16

Kinetic Product

26:17

Structure Analysis Using Hofmann Elimination

28:22

Structure Analysis Using Hofmann Elimination

28:23

Biological Activity of Amines

30:30

Adrenaline

31:07

Mescaline (Peyote Alkaloid)

31:22

Amino Acids, Amide, and Protein

32:14

Biological Activity of Amines

32:50

Morphine (Opium Alkaloid)

32:51

Epibatidine (Poison Dart Frog)

33:28

Nicotine

33:48

Choline (Nerve Impulse)

34:03

Section 11: Biomolecules & Polymers

Biomolecules

1h 53m 20s

Intro

0:00

Carbohydrates

1:11

D-glucose Overview

1:12

D-glucose: Cyclic Form (6-membered ring)

4:31

Cyclic Forms of Glucose: 6-membered Ring

8:24

α-D-glucopyranose & β-D-glucopyranose

8:25

Formation of a 5-Membered Ring

11:05

D-glucose: Formation of a 5-Membered Ring

11:06

Cyclic Forms of Glucose: 5-membered Ring

12:37

α-D-glucofuranose & β-D-glucofuranose

12:38

Carbohydrate Mechanism

14:03

Carbohydrate Mechanism

14:04

Reactions of Glucose: Acetal Formation

21:35

Acetal Formation: Methyl-α-D-glucoside

21:36

Hemiacetal to Acetal: Overview

24:58

Mechanism for Formation of Glycosidic Bond

25:51

Hemiacetal to Acetal: Mechanism

25:52

Formation of Disaccharides

29:34

Formation of Disaccharides

29:35

Some Polysaccharides: Starch

31:33

Amylose & Amylopectin

31:34

Starch: α-1,4-glycosidic Bonds

32:22

Properties of Starch Molecule

33:21

Some Polysaccharides: Cellulose

33:59

Cellulose: β-1,4-glycosidic bonds

34:00

Properties of Cellulose

34:59

Other Sugar-Containing Biomolecules

35:50

Ribonucleoside (RNA)

35:51

Deoxyribonucleoside (DMA)

36:59

Amino Acids & Proteins

37:32

α-amino Acids: Structure & Stereochemistry

37:33

Making a Protein (Condensation)

42:46

Making a Protein (Condensation)

42:47

Peptide Bond is Planar (Amide Resonance)

44:55

Peptide Bond is Planar (Amide Resonance)

44:56

Protein Functions

47:49

Muscle, Skin, Bones, Hair Nails

47:50

Enzymes

49:10

Antibodies

49:44

Hormones, Hemoglobin

49:58

Gene Regulation

50:20

Various Amino Acid Side Chains

50:51

Nonpolar

50:52

Polar

51:15

Acidic

51:24

Basic

51:55

Amino Acid Table

52:22

Amino Acid Table

52:23

Isoelectric Point (pI)

53:43

Isoelectric Point (pI) of Glycine

53:44

Isoelectric Point (pI) of Glycine: pH 11

56:42

Isoelectric Point (pI) of Glycine: pH 1

57:20

Isoelectric Point (pI), cont.

58:05

Asparatic Acid

58:06

Histidine

1:00:28

Isoelectric Point (pI), cont.

1:02:54

Example: What is the Net Charge of This Tetrapeptide at pH 6.0?

1:02:55

Nucleic Acids: Ribonucleosides

1:10:32

Nucleic Acids: Ribonucleosides

1:10:33

Nucleic Acids: Ribonucleotides

1:11:48

Ribonucleotides: 5' Phosphorylated Ribonucleosides

1:11:49

Ribonucleic Acid (RNA) Structure

1:12:35

Ribonucleic Acid (RNA) Structure

1:12:36

Nucleic Acids: Deoxyribonucleosides

1:14:08

Nucleic Acids: Deoxyribonucleosides

1:14:09

Deoxythymidine (T)

1:14:36

Nucleic Acids: Base-Pairing

1:15:17

Nucleic Acids: Base-Pairing

1:15:18

Double-Stranded Structure of DNA

1:18:16

Double-Stranded Structure of DNA

1:18:17

Model of DNA

1:19:40

Model of DNA

1:19:41

Space-Filling Model of DNA

1:20:46

Space-Filling Model of DNA

1:20:47

Function of RNA and DNA

1:23:06

DNA & Transcription

1:23:07

RNA & Translation

1:24:22

Genetic Code

1:25:09

Genetic Code

1:25:10

Lipids/Fats/Triglycerides

1:27:10

Structure of Glycerol

1:27:43

Saturated & Unsaturated Fatty Acids

1:27:51

Triglyceride

1:28:43

Unsaturated Fats: Lower Melting Points (Liquids/Oils)

1:29:15

Saturated Fat

1:29:16

Unsaturated Fat

1:30:10

Partial Hydrogenation

1:32:05

Saponification of Fats

1:35:11

Saponification of Fats

1:35:12

History of Soap

1:36:50

Carboxylate Salts form Micelles in Water

1:41:02

Carboxylate Salts form Micelles in Water

1:41:03

Cleaning Power of Micelles

1:42:21

Cleaning Power of Micelles

1:42:22

3-D Image of a Micelle

1:42:58

3-D Image of a Micelle

1:42:59

Synthesis of Biodiesel

1:44:04

Synthesis of Biodiesel

1:44:05

Phosphoglycerides

1:47:54

Phosphoglycerides

1:47:55

Cell Membranes Contain Lipid Bilayers

1:48:41

Cell Membranes Contain Lipid Bilayers

1:48:42

Bilayer Acts as Barrier to Movement In/Out of Cell

1:50:24

Bilayer Acts as Barrier to Movement In/Out of Cell

1:50:25

Organic Chemistry Meets Biology… Biochemistry!

1:51:12

Organic Chemistry Meets Biology… Biochemistry!

1:51:13

Polymers

45m 47s

Intro

0:00

Polymers

0:05

Monomer to Polymer: Vinyl Chloride to Polyvinyl Chloride

0:06

Polymer Properties

1:32

Polymer Properties

1:33

Natural Polymers: Rubber

2:30

Vulcanization

2:31

Natural Polymers: Polysaccharides

4:55

Example: Starch

4:56

Example: Cellulose

5:45

Natural Polymers: Proteins

6:07

Example: Keratin

6:08

DNA Strands

7:15

DNA Strands

7:16

Synthetic Polymers

8:30

Ethylene & Polyethylene: Lightweight Insulator & Airtight Plastic

8:31

Synthetic Organic Polymers

12:22

Polyethylene

12:28

Polyvinyl Chloride (PVC)

12:54

Polystyrene

13:28

Polyamide

14:34

Polymethyl Methacrylate

14:57

Kevlar

15:25

Synthetic Material Examples

16:30

How are Polymers Made?

21:00

Chain-growth Polymers Additions to Alkenes can be Radical, Cationic or Anionic

21:01

Chain Branching

22:34

Chain Branching

22:35

Special Reaction Conditions Prevent Branching

24:28

Ziegler-Natta Catalyst

24:29

Chain-Growth by Cationic Polymerization

27:35

Chain-Growth by Cationic Polymerization

27:36

Chain-Growth by Anionic Polymerization

29:35

Chain-Growth by Anionic Polymerization

29:36

Step-Growth Polymerization: Polyamides

32:16

Step-Growth Polymerization: Polyamides

32:17

Step-Growth Polymerization: Polyesters

34:23

Step-Growth Polymerization: Polyesters

34:24

Step-Growth Polymerization: Polycarbonates

35:56

Step-Growth Polymerization: Polycarbonates

35:57

Step-Growth Polymerization: Polyurethanes

37:18

Step-Growth Polymerization: Polyurethanes

37:19

Modifying Polymer Properties

39:35

Glass Transition Temperature

40:04

Crosslinking

40:42

Copolymers

40:58

Additives: Stabilizers

42:08

Additives: Flame Retardants

43:03

Additives: Plasticizers

43:41

Additives: Colorants

44:54

Section 12: Organic Synthesis

Organic Synthesis Strategies

2h 20m 24s

Intro

0:00

Organic Synthesis Strategies

0:15

Goal

0:16

Strategy

0:29

Example of a RetroSynthesis

1:30

Finding Starting Materials for Target Molecule

1:31

Synthesis Using Starting Materials

4:56

Synthesis of Alcohols by Functional Group Interconversion (FGI)

6:00

Synthesis of Alcohols by Functional Group Interconversion Overview

6:01

Alcohols by Reduction

7:43

Ketone to Alcohols

7:45

Aldehyde to Alcohols

8:26

Carboxylic Acid Derivative to Alcohols

8:36

Alcohols by Hydration of Alkenes

9:28

Hydration of Alkenes Using H₃O⁺

9:29

Oxymercuration-Demercuration

10:35

Hydroboration Oxidation

11:02

Alcohols by Substitution

11:42

Primary Alkyl Halide to Alcohols Using NaOH

11:43

Secondary Alkyl Halide to Alcohols Using Sodium Acetate

13:07

Tertiary Alkyl Halide to Alcohols Using H₂O

15:08

Synthesis of Alcohols by Forming a New C-C Bond

15:47

Recall: Alcohol & RMgBr

15:48

Retrosynthesis

17:28

Other Alcohol Disconnections

19:46

19:47

Synthesis Using PhMGgBr: Example 2

23:05

Synthesis of Alkyl Halides

26:06

Synthesis of Alkyl Halides Overview

26:07

Synthesis of Alkyl Halides by Free Radical Halogenation

27:04

Synthesis of Alkyl Halides by Free Radical Halogenation

27:05

Synthesis of Alkyl Halides by Substitution

29:06

Alcohol to Alkyl Halides Using HBr or HCl

29:07

Alcohol to Alkyl Halides Using SOCl₂

30:57

Alcohol to Alkyl Halides Using PBr₃ and Using P, I₂

31:03

Synthesis of Alkyl Halides by Addition

32:02

Alkene to Alkyl Halides Using HBr

32:03

Alkene to Alkyl Halides Using HBr & ROOR (Peroxides)

32:35

Example: Synthesis of Alkyl Halide

34:18

Example: Synthesis of Alkyl Halide

34:19

Synthesis of Ethers

39:25

Synthesis of Ethers

39:26

Example: Synthesis of an Ether

41:12

Synthesize TBME (t-butyl methyl ether) from Alcohol Starting Materials

41:13

Synthesis of Amines

46:05

Synthesis of Amines

46:06

Gabriel Synthesis of Amines

47:57

Gabriel Synthesis of Amines

47:58

Amines by SN2 with Azide Nu:

49:50

Amines by SN2 with Azide Nu:

49:51

Amines by SN2 with Cyanide Nu:

50:31

Amines by SN2 with Cyanide Nu:

50:32

Amines by Reduction of Amides

51:30

Amines by Reduction of Amides

51:31

Reductive Amination of Ketones/Aldehydes

52:42

Reductive Amination of Ketones/Aldehydes

52:43

Example : Synthesis of an Amine

53:47

Example 1: Synthesis of an Amine

53:48

Example 2: Synthesis of an Amine

56:16

Synthesis of Alkenes

58:20

Synthesis of Alkenes Overview

58:21

Synthesis of Alkenes by Elimination

59:04

Synthesis of Alkenes by Elimination Using NaOH & Heat

59:05

Synthesis of Alkenes by Elimination Using H₂SO₄ & Heat

59:57

Synthesis of Alkenes by Reduction

1:02:05

Alkyne to Cis Alkene

1:02:06

Alkyne to Trans Alkene

1:02:56

Synthesis of Alkenes by Wittig Reaction

1:03:46

Synthesis of Alkenes by Wittig Reaction

1:03:47

Retrosynthesis of an Alkene

1:05:35

Example: Synthesis of an Alkene

1:06:57

Example: Synthesis of an Alkene

1:06:58

Making a Wittig Reagent

1:10:31

Synthesis of Alkynes

1:13:09

Synthesis of Alkynes

1:13:10

Synthesis of Alkynes by Elimination (FGI)

1:13:42

First Step: Bromination of Alkene

1:13:43

Second Step: KOH Heat

1:14:22

Synthesis of Alkynes by Alkylation

1:15:02

Synthesis of Alkynes by Alkylation

1:15:03

Retrosynthesis of an Alkyne

1:16:18

Example: Synthesis of an Alkyne

1:17:40

Example: Synthesis of an Alkyne

1:17:41

Synthesis of Alkanes

1:20:52

Synthesis of Alkanes

1:20:53

Synthesis of Aldehydes & Ketones

1:21:38

Oxidation of Alcohol Using PCC or Swern

1:21:39

Oxidation of Alkene Using 1) O₃, 2)Zn

1:22:42

Reduction of Acid Chloride & Nitrile Using DiBAL-H

1:23:25

Hydration of Alkynes

1:24:55

Synthesis of Ketones by Acyl Substitution

1:26:12

Reaction with R'₂CuLi

1:26:13

Reaction with R'MgBr

1:27:13

Synthesis of Aldehydes & Ketones by α-Alkylation

1:28:00

Synthesis of Aldehydes & Ketones by α-Alkylation

1:28:01

Retrosynthesis of a Ketone

1:30:10

Acetoacetate Ester Synthesis of Ketones

1:31:05

Acetoacetate Ester Synthesis of Ketones: Step 1

1:31:06

Acetoacetate Ester Synthesis of Ketones: Step 2

1:32:13

Acetoacetate Ester Synthesis of Ketones: Step 3

1:32:50

Example: Synthesis of a Ketone

1:34:11

Example: Synthesis of a Ketone

1:34:12

Synthesis of Carboxylic Acids

1:37:15

Synthesis of Carboxylic Acids

1:37:16

Example: Synthesis of a Carboxylic Acid

1:37:59

Example: Synthesis of a Carboxylic Acid (Option 1)

1:38:00

Example: Synthesis of a Carboxylic Acid (Option 2)

1:40:51

Malonic Ester Synthesis of Carboxylic Acid

1:42:34

Malonic Ester Synthesis of Carboxylic Acid: Step 1

1:42:35

Malonic Ester Synthesis of Carboxylic Acid: Step 2

1:43:36

Malonic Ester Synthesis of Carboxylic Acid: Step 3

1:44:01

Example: Synthesis of a Carboxylic Acid

1:44:53

Example: Synthesis of a Carboxylic Acid

1:44:54

Synthesis of Carboxylic Acid Derivatives

1:48:05

Synthesis of Carboxylic Acid Derivatives

1:48:06

Alternate Ester Synthesis

1:48:58

Using Fischer Esterification

1:48:59

Using SN2 Reaction

1:50:18

Using Diazomethane

1:50:56

Using 1) LDA, 2) R'-X

1:52:15

Practice: Synthesis of an Alkyl Chloride

1:53:11

Practice: Synthesis of an Alkyl Chloride

1:53:12

Patterns of Functional Groups in Target Molecules

1:59:53

Recall: Aldol Reaction

1:59:54

β-hydroxy Ketone Target Molecule

2:01:12

α,β-unsaturated Ketone Target Molecule

2:02:20

Patterns of Functional Groups in Target Molecules

2:03:15

Recall: Michael Reaction

2:03:16

Retrosynthesis: 1,5-dicarbonyl Target Molecule

2:04:07

Patterns of Functional Groups in Target Molecules

2:06:38

Recall: Claisen Condensation

2:06:39

Retrosynthesis: β-ketoester Target Molecule

2:07:30

2-Group Target Molecule Summary

2:09:03

2-Group Target Molecule Summary

2:09:04

Example: Synthesis of Epoxy Ketone

2:11:19

Synthesize the Following Target Molecule from Cyclohexanone: Part 1 - Retrosynthesis

2:11:20

Synthesize the Following Target Molecule from Cyclohexanone: Part 2 - Synthesis

2:14:10

Example: Synthesis of a Diketone

2:16:57

Synthesis of a Diketone: Step 1 - Retrosynthesis

2:16:58

Synthesis of a Diketone: Step 2 - Synthesis

2:18:51

Section 12: Organic Synthesis & Organic Analysis

Organic Analysis: Classical & Modern Methods

46m 46s

Intro

0:00