Intro
0:00Organic Synthesis Strategies
0:15Goal
0:16Strategy
0:29
Example of a RetroSynthesis
1:30Finding Starting Materials for Target Molecule
1:31Synthesis Using Starting Materials
4:56
Synthesis of Alcohols by Functional Group Interconversion (FGI)
6:00Synthesis of Alcohols by Functional Group Interconversion Overview
6:01
Alcohols by Reduction
7:43Ketone to Alcohols
7:45Aldehyde to Alcohols
8:26Carboxylic Acid Derivative to Alcohols
8:36
Alcohols by Hydration of Alkenes
9:28Hydration of Alkenes Using H₃O⁺
9:29Oxymercuration-Demercuration
10:35Hydroboration Oxidation
11:02
Alcohols by Substitution
11:42Primary Alkyl Halide to Alcohols Using NaOH
11:43Secondary Alkyl Halide to Alcohols Using Sodium Acetate
13:07Tertiary Alkyl Halide to Alcohols Using H₂O
15:08
Synthesis of Alcohols by Forming a New C-C Bond
15:47Recall: Alcohol & RMgBr
15:48Retrosynthesis
17:28
Other Alcohol Disconnections
19:46
19:47Synthesis Using PhMGgBr: Example 2
23:05
Synthesis of Alkyl Halides
26:06Synthesis of Alkyl Halides Overview
26:07
Synthesis of Alkyl Halides by Free Radical Halogenation
27:04Synthesis of Alkyl Halides by Free Radical Halogenation
27:05
Synthesis of Alkyl Halides by Substitution
29:06Alcohol to Alkyl Halides Using HBr or HCl
29:07Alcohol to Alkyl Halides Using SOCl₂
30:57Alcohol to Alkyl Halides Using PBr₃ and Using P, I₂
31:03
Synthesis of Alkyl Halides by Addition
32:02Alkene to Alkyl Halides Using HBr
32:03Alkene to Alkyl Halides Using HBr & ROOR (Peroxides)
32:35
Example: Synthesis of Alkyl Halide
34:18Example: Synthesis of Alkyl Halide
34:19
Synthesis of Ethers
39:25Synthesis of Ethers
39:26
Example: Synthesis of an Ether
41:12Synthesize TBME (t-butyl methyl ether) from Alcohol Starting Materials
41:13
Synthesis of Amines
46:05Synthesis of Amines
46:06
Gabriel Synthesis of Amines
47:57Gabriel Synthesis of Amines
47:58
Amines by SN2 with Azide Nu:
49:50Amines by SN2 with Azide Nu:
49:51
Amines by SN2 with Cyanide Nu:
50:31Amines by SN2 with Cyanide Nu:
50:32
Amines by Reduction of Amides
51:30Amines by Reduction of Amides
51:31
Reductive Amination of Ketones/Aldehydes
52:42Reductive Amination of Ketones/Aldehydes
52:43
Example : Synthesis of an Amine
53:47Example 1: Synthesis of an Amine
53:48Example 2: Synthesis of an Amine
56:16
Synthesis of Alkenes
58:20Synthesis of Alkenes Overview
58:21
Synthesis of Alkenes by Elimination
59:04Synthesis of Alkenes by Elimination Using NaOH & Heat
59:05Synthesis of Alkenes by Elimination Using H₂SO₄ & Heat
59:57
Synthesis of Alkenes by Reduction
1:02:05Alkyne to Cis Alkene
1:02:06Alkyne to Trans Alkene
1:02:56
Synthesis of Alkenes by Wittig Reaction
1:03:46Synthesis of Alkenes by Wittig Reaction
1:03:47Retrosynthesis of an Alkene
1:05:35
Example: Synthesis of an Alkene
1:06:57Example: Synthesis of an Alkene
1:06:58Making a Wittig Reagent
1:10:31
Synthesis of Alkynes
1:13:09Synthesis of Alkynes
1:13:10
Synthesis of Alkynes by Elimination (FGI)
1:13:42First Step: Bromination of Alkene
1:13:43Second Step: KOH Heat
1:14:22
Synthesis of Alkynes by Alkylation
1:15:02Synthesis of Alkynes by Alkylation
1:15:03Retrosynthesis of an Alkyne
1:16:18
Example: Synthesis of an Alkyne
1:17:40Example: Synthesis of an Alkyne
1:17:41
Synthesis of Alkanes
1:20:52Synthesis of Alkanes
1:20:53
Synthesis of Aldehydes & Ketones
1:21:38Oxidation of Alcohol Using PCC or Swern
1:21:39Oxidation of Alkene Using 1) O₃, 2)Zn
1:22:42Reduction of Acid Chloride & Nitrile Using DiBAL-H
1:23:25Hydration of Alkynes
1:24:55Synthesis of Ketones by Acyl Substitution
1:26:12Reaction with R'₂CuLi
1:26:13Reaction with R'MgBr
1:27:13
Synthesis of Aldehydes & Ketones by α-Alkylation
1:28:00Synthesis of Aldehydes & Ketones by α-Alkylation
1:28:01Retrosynthesis of a Ketone
1:30:10
Acetoacetate Ester Synthesis of Ketones
1:31:05Acetoacetate Ester Synthesis of Ketones: Step 1
1:31:06Acetoacetate Ester Synthesis of Ketones: Step 2
1:32:13Acetoacetate Ester Synthesis of Ketones: Step 3
1:32:50
Example: Synthesis of a Ketone
1:34:11Example: Synthesis of a Ketone
1:34:12
Synthesis of Carboxylic Acids
1:37:15Synthesis of Carboxylic Acids
1:37:16
Example: Synthesis of a Carboxylic Acid
1:37:59Example: Synthesis of a Carboxylic Acid (Option 1)
1:38:00Example: Synthesis of a Carboxylic Acid (Option 2)
1:40:51
Malonic Ester Synthesis of Carboxylic Acid
1:42:34Malonic Ester Synthesis of Carboxylic Acid: Step 1
1:42:35Malonic Ester Synthesis of Carboxylic Acid: Step 2
1:43:36Malonic Ester Synthesis of Carboxylic Acid: Step 3
1:44:01
Example: Synthesis of a Carboxylic Acid
1:44:53Example: Synthesis of a Carboxylic Acid
1:44:54
Synthesis of Carboxylic Acid Derivatives
1:48:05Synthesis of Carboxylic Acid Derivatives
1:48:06
Alternate Ester Synthesis
1:48:58Using Fischer Esterification
1:48:59Using SN2 Reaction
1:50:18Using Diazomethane
1:50:56Using 1) LDA, 2) R'-X
1:52:15
Practice: Synthesis of an Alkyl Chloride
1:53:11Practice: Synthesis of an Alkyl Chloride
1:53:12
Patterns of Functional Groups in Target Molecules
1:59:53Recall: Aldol Reaction
1:59:54β-hydroxy Ketone Target Molecule
2:01:12α,β-unsaturated Ketone Target Molecule
2:02:20
Patterns of Functional Groups in Target Molecules
2:03:15Recall: Michael Reaction
2:03:16Retrosynthesis: 1,5-dicarbonyl Target Molecule
2:04:07
Patterns of Functional Groups in Target Molecules
2:06:38Recall: Claisen Condensation
2:06:39Retrosynthesis: β-ketoester Target Molecule
2:07:30
2-Group Target Molecule Summary
2:09:032-Group Target Molecule Summary
2:09:04
Example: Synthesis of Epoxy Ketone
2:11:19Synthesize the Following Target Molecule from Cyclohexanone: Part 1 - Retrosynthesis
2:11:20Synthesize the Following Target Molecule from Cyclohexanone: Part 2 - Synthesis
2:14:10
Example: Synthesis of a Diketone
2:16:57Synthesis of a Diketone: Step 1 - Retrosynthesis
2:16:58Synthesis of a Diketone: Step 2 - Synthesis
2:18:51
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