Chemistry: Organic Chemistry Lab Dr. Laurie Starkey, Ph.D.
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Level Intermediate
16 Lessons (17hr : 07min)
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Audio: English
English

Dr. Laurie Starkey brings her expertise in Organic Chemistry to help students learn important laboratory theory and techniques. She covers everything from melting point, distillation, and extraction, to more advanced concepts in chromatography and spectroscopy. Each lesson contains all the necessary steps to correctly assemble the apparatus and complete the experiment, followed by a comprehensive pre-lab discussion of theory, procedures, and calculations. This course is crucial for students who wish to excel in Organic Chemistry Laboratory in order to satisfy their degree or pre-medical requirements. Dr. Laurie Starkey is the author of “Introduction to Strategies for Organic Synthesis” (Wiley) and earned her Ph.D. in Chemistry from UCLA. She has been teaching Organic Chemistry at the university level for over 20 years and most recently won the 2013 Provost's Award for Excellence in Teaching, Cal Poly Pomona's highest teaching award.

Table of Contents
Course Details

Section 1: Reagent Table
	Completing the Reagent Table for Prelab			21:09
		Intro		0:00
		Sample Reagent Table		0:11
			Reagent Table Overview	0:12
			Calculate Moles of 2-bromoaniline	6:44
		Calculate Molar Amounts of Each Reagent		9:20
			Calculate Mole of NaNO₂	9:21
			Calculate Moles of KI	10:33
		Identify the Limiting Reagent		11:17
			Which Reagent is the Limiting Reagent?	11:18
		Calculate Molar Equivalents		13:37
			Molar Equivalents	13:38
		Calculate Theoretical Yield		16:40
			Theoretical Yield	16:41
		Calculate Actual Yield (%Yield)		18:30
			Actual Yield (%Yield)	18:31
Section 2: Melting Points
	Introduction to Melting Points			16:10
		Intro		0:00
		Definition of a Melting Point (mp)		0:04
			Definition of a Melting Point (mp)	0:05
			Solid Samples Melt Gradually	1:49
			Recording Range of Melting Temperature	2:04
		Melting Point Theory		3:14
			Melting Point Theory	3:15
		Effects of Impurities on a Melting Point		3:57
			Effects of Impurities on a Melting Point	3:58
			Special Exception: Eutectic Mixtures	5:09
			Freezing Point Depression by Solutes	5:39
		Melting Point Uses		6:19
			Solid Compound	6:20
			Determine Purity of a Sample	6:42
			Identify an Unknown Solid	7:06
		Recording a Melting Point		9:03
			Pack 1-3 mm of Dry Powder in MP Tube	9:04
			Slowly Heat Sample	9:55
			Record Temperature at First Sign of Melting	10:33
			Record Temperature When Last Crystal Disappears	11:26
			Discard MP Tube in Glass Waste	11:32
			Determine Approximate MP	11:42
		Tips, Tricks and Warnings		12:28
			Use Small, Tightly Packed Sample	12:29
			Be Sure MP Apparatus is Cool	12:45
			Never Reuse a MP Tube	13:16
			Sample May Decompose	13:30
			If Pure Melting Point (MP) Doesn't Match Literature	14:20
	Melting Point Lab			8:17
		Intro		0:00
		Melting Point Tubes		0:40
		Melting Point Apparatus		3:42
		Recording a melting Point		5:50
Section 3: Recrystallization
	Introduction to Recrystallization			22:00
		Intro		0:00
		Crystallization to Purify a Solid		0:10
			Crude Solid	0:11
			Hot Solution	0:20
			Crystals	1:09
			Supernatant Liquid	1:20
		Theory of Crystallization		2:34
			Theory of Crystallization	2:35
		Analysis and Obtaining a Second Crop		3:40
			Crystals → Melting Point, TLC	3:41
			Supernatant Liquid → Crude Solid → Pure Solid	4:18
			Crystallize Again → Pure Solid (2nd Crop)	4:32
		Choosing a Solvent		5:19
			1. Product is Very Soluble at High Temperatures	5:20
			2. Product has Low Solubility at Low Temperatures	6:00
			3. Impurities are Soluble at All Temperatures	6:16
			Check Handbooks for Suitable Solvents	7:33
		Why Isn't This Dissolving?!		8:46
			If Solid Remains When Solution is Hot	8:47
			Still Not Dissolved in Hot Solvent?	10:18
		Where Are My Crystals?!		12:23
			If No Crystals Form When Solution is Cooled	12:24
			Still No Crystals?	14:59
		Tips, Tricks and Warnings		16:26
			Always Use a Boiling Chip or Stick!	16:27
			Use Charcoal to Remove Colored Impurities	16:52
			Solvent Pairs May Be Used	18:23
			Product May 'Oil Out'	20:11
	Recrystallization Lab			19:07
		Intro		0:00
		Step 1: Dissolving the Solute in the Solvent		0:12
		Hot Filtration		6:33
		Step 2: Cooling the Solution		8:01
		Step 3: Filtering the Crystals		12:08
		Step 4: Removing & Drying the Crystals		16:10
Section 4: Distillation
	Introduction to Distillation			25:54
		Intro		0:00
		Distillation: Purify a Liquid		0:04
			Simple Distillation	0:05
			Fractional Distillation	0:55
		Theory of Distillation		1:04
			Theory of Distillation	1:05
		Vapor Pressure and Volatility		1:52
			Vapor Pressure	1:53
			Volatile Liquid	2:28
			Less Volatile Liquid	3:09
		Vapor Pressure vs. Boiling Point		4:03
			Vapor Pressure vs. Boiling Point	4:04
			Increasing Vapor Pressure	4:38
		The Purpose of Boiling Chips		6:46
			The Purpose of Boiling Chips	6:47
		Homogeneous Mixtures of Liquids		9:24
			Dalton's Law	9:25
			Raoult's Law	10:27
		Distilling a Mixture of Two Liquids		11:41
			Distilling a Mixture of Two Liquids	11:42
		Simple Distillation: Changing Vapor Composition		12:06
			Vapor & Liquid	12:07
			Simple Distillation: Changing Vapor Composition	14:47
			Azeotrope	18:41
		Fractional Distillation: Constant Vapor Composition		19:42
			Fractional Distillation: Constant Vapor Composition	19:43
	Distillation Lab			24:13
		Intro		0:00
		Glassware Overview		0:04
		Heating a Sample		3:09
			Bunsen Burner	3:10
			Heating Mantle 1	4:45
			Heating Mantle 2	6:18
			Hot Plate	7:10
		Simple Distillation Lab		8:37
		Fractional Distillation Lab		17:13
		Removing the Distillation Set-Up		22:41
Section 5: Chromatography
	Introduction to TLC (Thin-Layer Chromatography)			28:51
		Intro		0:00
		Chromatography		0:06
			Purification & Analysis	0:07
			Types of Chromatography: Thin-layer, Column, Gas, & High Performance Liquid	0:24
		Theory of Chromatography		0:44
			Theory of Chromatography	0:45
		Performing a Thin-layer Chromatography (TLC) Analysis		2:30
			Overview: Thin-layer Chromatography (TLC) Analysis	2:31
		Step 1: 'Spot' the TLC Plate		4:11
		Step 2: Prepare the Developing Chamber		5:54
		Step 3: Develop the TLC Plate		7:30
		Step 4: Visualize the Spots		9:02
		Step 5: Calculate the Rf for Each Spot		12:00
		Compound Polarity: Effect on Rf		16:50
			Compound Polarity: Effect on Rf	16:51
		Solvent Polarity: Effect on Rf		18:47
			Solvent Polarity: Effect on Rf	18:48
			Example: EtOAc & Hexane	19:35
		Other Types of Chromatography		22:27
			Thin-layer Chromatography (TLC)	22:28
			Column Chromatography	22:56
			High Performance Liquid (HPLC)	23:59
			Gas Chromatography (GC)	24:38
			Preparative 'prep' Scale Possible	28:05
	TLC Analysis Lab			20:50
		Intro		0:00
		Step 1: 'Spot' the TLC Plate		0:06
		Step 2: Prepare the Developing Chamber		4:06
		Step 3: Develop the TLC Plate		6:26
		Step 4: Visualize the Spots		7:45
		Step 5: Calculate the Rf for Each Spot		11:48
		How to Make Spotters		12:58
		TLC Plate		16:04
		Flash Column Chromatography		17:11
Section 6: Extractions
	Introduction to Extractions			34:25
		Intro		0:00
		Extraction Purify, Separate Mixtures		0:07
			Adding a Second Solvent	0:28
			Mixing Two Layers	0:38
			Layers Settle	0:54
			Separate Layers	1:05
		Extraction Uses		1:20
			To Separate Based on Difference in Solubility/Polarity	1:21
			To Separate Based on Differences in Reactivity	2:11
			Separate & Isolate	2:20
		Theory of Extraction		3:03
			Aqueous & Organic Phases	3:04
			Solubility: 'Like Dissolves Like'	3:25
			Separation of Layers	4:06
			Partitioning	4:14
		Distribution Coefficient, K		5:03
			Solutes Partition Between Phases	5:04
			Distribution Coefficient, K at Equilibrium	6:27
		Acid-Base Extractions		8:09
			Organic Layer	8:10
			Adding Aqueous HCl & Mixing Two Layers	8:46
			Neutralize (Adding Aqueous NaOH)	10:05
			Adding Organic Solvent Mix Two Layers 'Back Extract'	10:24
			Final Results	10:43
		Planning an Acid-Base Extraction, Part 1		11:01
			Solute Type: Neutral	11:02
			Aqueous Solution: Water	13:40
			Solute Type: Basic	14:43
			Solute Type: Weakly Acidic	15:23
			Solute Type: Acidic	16:12
		Planning an Acid-Base Extraction, Part 2		17:34
			Planning an Acid-Base Extraction	17:35
		Performing an Extraction		19:34
			Pour Solution into Sep Funnel	19:35
			Add Second Liquid	20:07
			Add Stopper, Cover with Hand, Remove from Ring	20:48
			Tip Upside Down, Open Stopcock to Vent Pressure	21:00
			Shake to Mix Two Layers	21:30
			Remove Stopper & Drain Bottom Layer	21:40
		Reaction Work-up: Purify, Isolate Product		22:03
			Typical Reaction is Run in Organic Solvent	22:04
			Starting a Reaction Work-up	22:33
			Extracting the Product with Organic Solvent	23:17
			Combined Extracts are Washed	23:40
			Organic Layer is 'Dried'	24:23
		Finding the Product		26:38
			Which Layer is Which?	26:39
			Where is My Product?	28:00
		Tips, Tricks and Warnings		29:29
			Leaking Sep Funnel	29:30
			Caution When Mixing Layers & Using Ether	30:17
			If an Emulsion Forms	31:51
	Extraction Lab			14:49
		Intro		0:00
		Step 1: Preparing the Separatory Funnel		0:03
		Step 2: Adding Sample		1:18
		Step 3: Mixing the Two Layers		2:59
		Step 4: Draining the Bottom Layers		4:59
		Step 5: Performing a Second Extraction		5:50
		Step 6: Drying the Organic Layer		7:21
		Step 7: Gravity Filtration		9:35
		Possible Extraction Challenges		12:55
Section 7: Spectroscopy
	Infrared Spectroscopy, Part I			1:04:00
		Intro		0:00
		Infrared (IR) Spectroscopy		0:09
			Introduction to Infrared (IR) Spectroscopy	0:10
			Intensity of Absorption Is Proportional to Change in Dipole	3:08
		IR Spectrum of an Alkane		6:08
			Pentane	6:09
		IR Spectrum of an Alkene		13:12
			1-Pentene	13:13
		IR Spectrum of an Alkyne		15:49
			1-Pentyne	15:50
		IR Spectrum of an Aromatic Compound		18:2
			Methylbenzene	18:24
		IR of Substituted Aromatic Compounds		24:04
			IR of Substituted Aromatic Compounds	24:05
		IR Spectrum of 1,2-Disubstituted Aromatic		25:30
			1,2-dimethylbenzene	25:31
		IR Spectrum of 1,3-Disubstituted Aromatic		27:15
			1,3-dimethylbenzene	27:16
		IR Spectrum of 1,4-Disubstituted Aromatic		28:41
			1,4-dimethylbenzene	28:42
		IR Spectrum of an Alcohol		29:34
			1-pentanol	29:35
		IR Spectrum of an Amine		32:39
			1-butanamine	32:40
		IR Spectrum of a 2° Amine		34:50
			Diethylamine	34:51
		IR Spectrum of a 3° Amine		35:47
			Triethylamine	35:48
		IR Spectrum of a Ketone		36:41
			2-butanone	36:42
		IR Spectrum of an Aldehyde		40:10
			Pentanal	40:11
		IR Spectrum of an Ester		42:38
			Butyl Propanoate	42:39
		IR Spectrum of a Carboxylic Acid		44:26
			Butanoic Acid	44:27
		Sample IR Correlation Chart		47:36
			Sample IR Correlation Chart: Wavenumber and Functional Group	47:37
		Predicting IR Spectra: Sample Structures		52:06
			Example 1	52:07
			Example 2	53:29
			Example 3	54:40
			Example 4	57:08
			Example 5	58:31
			Example 6	59:07
			Example 7	60:52
			Example 8	62:20
	Infrared Spectroscopy, Part II			48:34
		Intro		0:00
		Interpretation of IR Spectra: a Basic Approach		0:05
			Interpretation of IR Spectra: a Basic Approach	0:06
			Other Peaks to Look for	3:39
		Examples		5:17
			Example 1	5:18
			Example 2	9:09
			Example 3	11:52
			Example 4	14:03
			Example 5	16:31
			Example 6	19:31
			Example 7	22:32
			Example 8	24:39
		IR Problems Part 1		28:11
			IR Problem 1	28:12
			IR Problem 2	31:14
			IR Problem 3	32:59
			IR Problem 4	34:23
			IR Problem 5	35:49
			IR Problem 6	38:20
		IR Problems Part 2		42:36
			IR Problem 7	42:37
			IR Problem 8	44:02
			IR Problem 9	45:07
			IR Problems10	46:10
	Nuclear Magnetic Resonance (NMR) Spectroscopy, Part I			1:32:14
		Intro		0:00
		Purpose of NMR		0:14
			Purpose of NMR	0:15
		How NMR Works		2:17
			How NMR Works	2:18
		Information Obtained From a ¹H NMR Spectrum		5:51
			# of Signals, Integration, Chemical Shifts, and Splitting Patterns	5:52
		Number of Signals in NMR (Chemical Equivalence)		7:52
			Example 1: How Many Signals in ¹H NMR?	7:53
			Example 2: How Many Signals in ¹H NMR?	9:36
			Example 3: How Many Signals in ¹H NMR?	12:15
			Example 4: How Many Signals in ¹H NMR?	13:47
			Example 5: How Many Signals in ¹H NMR?	16:12
		Size of Signals in NMR (Peak Area or Integration)		21:23
			Size of Signals in NMR (Peak Area or Integration)	21:24
		Using Integral Trails		25:15
			Example 1: C₈H₁₈O	25:16
			Example 2: C₃H₈O	27:17
			Example 3: C₇H₈	28:21
		Location of NMR Signal (Chemical Shift)		29:05
			Location of NMR Signal (Chemical Shift)	29:06
		¹H NMR Chemical Shifts		33:20
			¹H NMR Chemical Shifts	33:21
		¹H NMR Chemical Shifts (Protons on Carbon)		37:03
			¹H NMR Chemical Shifts (Protons on Carbon)	37:04
		Chemical Shifts of H's on N or O		39:01
			Chemical Shifts of H's on N or O	39:02
		Estimating Chemical Shifts		41:13
			Example 1: Estimating Chemical Shifts	41:14
			Example 2: Estimating Chemical Shifts	43:22
			Functional Group Effects are Additive	45:28
		Calculating Chemical Shifts		47:38
			Methylene Calculation	47:39
			Methine Calculation	48:20
			Protons on sp³ Carbons: Chemical Shift Calculation Table	48:50
			Example: Estimate the Chemical Shift of the Selected H	50:29
		Effects of Resonance on Chemical Shifts		53:11
			Example 1: Effects of Resonance on Chemical Shifts	53:12
			Example 2: Effects of Resonance on Chemical Shifts	55:09
			Example 3: Effects of Resonance on Chemical Shifts	57:08
		Shape of NMR Signal (Splitting Patterns)		59:17
			Shape of NMR Signal (Splitting Patterns)	59:18
		Understanding Splitting Patterns: The 'n+1 Rule'		61:24
			Understanding Splitting Patterns: The 'n+1 Rule'	61:25
		Explanation of n+1 Rule		62:42
			Explanation of n+1 Rule: One Neighbor	62:43
			Explanation of n+1 Rule: Two Neighbors	66:23
		Summary of Splitting Patterns		66:24
			Summary of Splitting Patterns	70:45
		Predicting ¹H NMR Spectra		70:46
			Example 1: Predicting ¹H NMR Spectra	73:30
			Example 2: Predicting ¹H NMR Spectra	79:07
			Example 3: Predicting ¹H NMR Spectra	83:50
			Example 4: Predicting ¹H NMR Spectra	89:27
	Nuclear Magnetic Resonance (NMR) Spectroscopy, Part II			2:03:48
		Intro		0:00
		¹H NMR Problem-Solving Strategies		0:18
			Step 1: Analyze IR Spectrum (If Provided)	0:19
			Step 2: Analyze Molecular Formula (If Provided)	2:06
			Step 3: Draw Pieces of Molecule	3:49
			Step 4: Confirm Piecs	6:30
			Step 5: Put the Pieces Together!	7:23
			Step 6: Check Your Answer!	8:21
		Examples		9:17
			Example 1: Determine the Structure of a C₉H₁₀O₂ Compound with the Following ¹H NMR Data	9:18
			Example 2: Determine the Structure of a C₉H₁₀O₂ Compound with the Following ¹H NMR Data	17:27
		¹H NMR Practice		20:57
			¹H NMR Practice 1: C₁₀H₁₄	20:58
			¹H NMR Practice 2: C₄H₈O₂	29:50
			¹H NMR Practice 3: C₆H₁₂O₃	39:19
			¹H NMR Practice 4: C₈H₁₈	50:19
		More About Coupling Constants (J Values)		57:11
			Vicinal (3-bond) and Geminal (2-bond)	57:12
			Cyclohexane (ax-ax) and Cyclohexane (ax-eq) or (eq-eq)	59:50
			Geminal (Alkene), Cis (Alkene), and Trans (Alkene)	62:40
			Allylic (4-bond) and W-coupling (4-bond) (Rigid Structures Only)	64:05
		¹H NMR Advanced Splitting Patterns		65:39
			Example 1: ¹H NMR Advanced Splitting Patterns	65:40
			Example 2: ¹H NMR Advanced Splitting Patterns	70:01
			Example 3: ¹H NMR Advanced Splitting Patterns	73:45
		¹H NMR Practice		82:53
			¹H NMR Practice 5: C₁₁H₁₇N	82:54
			¹H NMR Practice 6: C₉H₁₀O	94:04
		¹³C NMR Spectroscopy		104:49
			¹³C NMR Spectroscopy	104:50
		¹³C NMR Chemical Shifts		107:24
			¹³C NMR Chemical Shifts Part 1	107:25
			¹³C NMR Chemical Shifts Part 2	108:59
		¹³C NMR Practice		110:16
			¹³C NMR Practice 1	110:17
			¹³C NMR Practice 2	118:30
	Mass Spectrometry			1:28:35
		Intro		0:00
		Introduction to Mass Spectrometry		0:37
			Uses of Mass Spectrometry: Molecular Mass	0:38
			Uses of Mass Spectrometry: Molecular Formula	1:04
			Uses of Mass Spectrometry: Structural Information	1:21
			Uses of Mass Spectrometry: In Conjunction with Gas Chromatography	2:03
		Obtaining a Mass Spectrum		2:59
			Obtaining a Mass Spectrum	3:00
		The Components of a Mass Spectrum		6:44
			The Components of a Mass Spectrum	6:45
		What is the Mass of a Single Molecule		12:13
			Example: CH₄	12:14
			Example: ¹³CH₄	12:51
			What Ratio is Expected for the Molecular Ion Peaks of C₂H₆?	14:20
		Other Isotopes of High Abundance		16:30
			Example: Cl Atoms	16:31
			Example: Br Atoms	18:33
			Mass Spectrometry of Chloroethane	19:22
			Mass Spectrometry of Bromobutane	21:23
		Isotopic Abundance can be Calculated		22:48
			What Ratios are Expected for the Molecular Ion Peaks of CH₂Br₂?	22:49
		Determining Molecular Formula from High-resolution Mass Spectrometry		26:53
			Exact Masses of Various Elements	26:54
		Fragmentation of various Functional Groups		28:42
			What is More Stable, a Carbocation C⁺ or a Radical R?	28:43
			Fragmentation is More Likely If It Gives Relatively Stable Carbocations and Radicals	31:37
		Mass Spectra of Alkanes		33:15
			Example: Hexane	33:16
			Fragmentation Method 1	34:19
			Fragmentation Method 2	35:46
			Fragmentation Method 3	36:15
		Mass of Common Fragments		37:07
			Mass of Common Fragments	37:08
		Mass Spectra of Alkanes		39:28
			Mass Spectra of Alkanes	39:29
			What are the Peaks at m/z 15 and 71 So Small?	41:01
		Branched Alkanes		43:12
			Explain Why the Base Peak of 2-methylhexane is at m/z 43 (M-57)	43:13
		Mass Spectra of Alkenes		45:42
			Mass Spectra of Alkenes: Remove 1 e⁻	45:43
			Mass Spectra of Alkenes: Fragment	46:14
			High-Energy Pi Electron is Most Likely Removed	47:59
		Mass Spectra of Aromatic Compounds		49:01
			Mass Spectra of Aromatic Compounds	49:02
		Mass Spectra of Alcohols		51:32
			Mass Spectra of Alcohols	51:33
		Mass Spectra of Ethers		54:53
			Mass Spectra of Ethers	54:54
		Mass Spectra of Amines		56:49
			Mass Spectra of Amines	56:50
		Mass Spectra of Aldehydes & Ketones		59:23
			Mass Spectra of Aldehydes & Ketones	59:24
		McLafferty Rearrangement		61:29
			McLafferty Rearrangement	61:30
		Mass Spectra of Esters		64:15
			Mass Spectra of Esters	61:16
		Mass Spectrometry Discussion I		65:01
			For the Given Molecule (M=58), Do You Expect the More Abundant Peak to Be m/z 15 or m/z 43?	65:02
		Mass Spectrometry Discussion II		68:13
			For the Given Molecule (M=74), Do You Expect the More Abundant Peak to Be m/z 31, m/z 45, or m/z 59?	68:14
		Mass Spectrometry Discussion III		71:42
			Explain Why the Mass Spectra of Methyl Ketones Typically have a Peak at m/z 43	71:43
		Mass Spectrometry Discussion IV		74:46
			In the Mass Spectrum of the Given Molecule (M=88), Account for the Peaks at m/z 45 and m/z 57	74:47
		Mass Spectrometry Discussion V		78:25
			How Could You Use Mass Spectrometry to Distinguish Between the Following Two Compounds (M=73)?	78:26
		Mass Spectrometry Discussion VI		82:45
			What Would be the m/z Ratio for the Fragment for the Fragment Resulting from a McLafferty Rearrangement for the Following Molecule (M=114)?	82:46