Spring 2010 – CHEM 2212 Organic Chemistry II – Daily Lesson Objectives
Alcohols, Phenols and Thiols; Ethers and Sulfides (Ch. 13)
Day 1 (1/11/10) – Introduction to CHEM 2212 / Start of Chapter 13
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Read Ch. 13.1 - 13.2
Problems before class: 13.1 - 5
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Videos to watch in preparation for class: naming alcohols
Name and draw the structures of alcohols, phenols and thiols
Describe trends in physical properties of alcohols, phenols and thiols
Demonstrate how alcohols are both weakly acidic and weakly basic
Draw resonance structures to explain the higher acidity of phenols vs alcohols
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Problems during and after class: 13.20, 24a-e, 25, 27, 50
 Lab Day 1 (1/13/10) – Lab Check In and CHEM 2212 Introduction
Day 2 (1/15/10)
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Read Ch. 13.3 - 13.4
Problems before class: 13.6 - 10, 34
Write reactions for the preparation of alcohols from carbonyl compounds
Write mechanisms for the acid-catalyzed dehydration of 3 alcohols (E1 mechanism) and the dehydration of
1 and 2 alcohols with POCl3 in pyridine (E2 mechanism)
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Problems during and after class: 13.38, 41, 45, 51, 52, 54, 70
 Lab Day 2 (1/20/10) - Experiment H Week 1 (Exp H Prelab Quiz) - Oxidation of 4-chlorobenzyl alcohol
Day 3 (1/22/10)
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Read Ch. 13.4 - 13.7
Problems before class: 13.11 - 14, 24f-I, 58
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Videos to watch in preparation for class: naming ethers sulfides,
Know reactions to convert alcohols into esters
Know reactions to oxidize alcohols
Write reactions for the preparation and reactions of thiols
Name and draw structures of ethers and sulfides
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Problems during and after class: 13.22, 31, 33, 36, 59
Day 4 (1/25/10) - Quiz #1
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Read Ch.13.8 - 13.9, 13.11
Problems before class: 13.15 - 19, 65
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Videos to watch in preparation for class: reactions of ethers; williamson ether synthesis
Write the mechanism of the Williamson Ether Synthesis
Write reactions for the preparation and reactions of ethers
Analyze alcohols, phenols and ethers using spectroscopy
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Problems during and after class: 13.29, 30, 39, 41, 48, 66, 69
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 Lab Day 3 (1/27/10) - Experiment H Week 2 - Oxidation of 4-chlorobenzyl alcohol
Aldehydes and Ketones; Nucleophilic Addition Reactions (Ch. 14)
Day 5 (1/29/10)
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Read Ch. 14.1 - 14.4
Problems before class: 14.1 - 5, 25a-e
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Videos to watch in preparation for class: naming aldehydes ketones
Name and draw structures of aldehydes and ketones
Know methods for formation of aldehydes and ketones
Know methods to oxidize aldehydes to carboxylic acids
Write the general mechanisms for nucleophilic addition to aldehydes and ketones
List the common neutral and negatively charged nucleophiles
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Problems during and after class: 14.22d, 25f-j, 26, 27, 30, 38, 42
Day 6 (2/1/10)
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Read Ch. 14.5 - 14.6, 14.9
Problems before class: 14.6, 14.7, 14.13, 14.29
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Videos to watch in preparation for class: grignard reactions; hydride reductions; wittig reaction
Write the mechanisms of both acid- and base-catalyzed hydration of aldehydes and ketones
Write the mechanism of nucleophilic addition of Grignard and Hydride reagents
Write the mechanism of nucleophilic addition of phosphorous ylides (the Wittig reaction)
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Problems during and after class: 14.30, 31, 32, 33, 44, 50,
 Lab Day 4 (2/3/10) - Experiment I Week 1 (Exp I Prelab Quiz) - Wittig Reaction
Day 7 (2/5/10)
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Read Ch. 14.7 - 14.8
Problems before class: 14.8, 14.10, 14.12
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Videos to watch in preparation for class: acetal formation; imine enamine formation
Write the mechanism of nucleophilic addition of 1 and 2 amines to yield imines and enamines
Write the mechanism of nucleophilic addition of alcohols to yield hemiacetals and acetals
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Problems during and after class: 14.9, 22a-c, 24, 34, 40
Day 8 (2/8/10) - Quiz #2
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Read Ch. 14.9, 14.11, 14.12
Problems before class: 14.16, 14.17, 14.21, 14.60c
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Videos to watch in preparation for class: Grignard reactions in organic synthesis
Write the mechanism for conjugate addition of nucleophiles to an α,β-unsaturated aldehyde or ketone
Analyze aldehydes and ketones using spectroscopy
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Problems during and after class: 14.54, 55, 56, 57, 60b,
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 Lab Day 5 (2/10/10) - Experiment I Week 2 - Wittig Reaction
Carboxylic Acids and Nitriles (Ch. 15)
Day 9 (2/12/10)
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Read Ch. 15.1 - 15.2, 15.4 - 15.5
Problems before class: 15.1, 2, 3, 6, 7, 9, 32
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Videos to watch in preparation for class: naming acids nitriles; carboxylic acid synthesis
Name and draw the structures of carboxylic acids and nitriles
Explain the acidity of carboxylic acids
Explain the substituent effect on acidity
Know reactions for preparation of carboxylic acids
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Problems during and after class: 15.14, 18, 21, 24, 33, 45
Day 10 (2/15/10)
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Read Ch. 15.6 - 15.7
Problems before class: 15.11, 26, 27
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Videos to watch in preparation for class: amide elimination
Know the general scheme of carboxylic acid reactions as outlined in Figure 15.2
Know the reactions of nitriles
Write the mechanism for the production of nitriles via the elimination of an amide using thionyl chloride
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Problems during and after class: 15.25, 37, 40, 41, 47
 Lab Day 6 (2/17/10) - Experiment J Week 1 (Exp J Prelab Quiz) - Fischer Esterification
Day 11 (2/19/10) - Quiz #3
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Read Ch. 15.7 - 15.8
Problems before class: 15.12, 15.13, 53
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Videos to watch in preparation for class: acidic hydrolysis of nitriles
Write the mechanism for acidic hydrolysis of a nitrile to yield an amide, and at higher temperatures, a
carboxylic acid
Analyze carboxylic acids and nitriles using spectroscopy
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Problems during and after class: 15.38, 43, 51, 52
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Carboxylic Acids Derivatives: Nucleophilic Acyl Substitution Reactions
(Ch. 16)
Day 12 (2/22/10)
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Read Ch. 16.1 - 16.2
Problems before class: 16.1a-g, 16.2a-g, 16.3 - 16.5
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Videos to watch in preparation for class: naming acid derivatives; reactivity of acid derivatives
Name and draw structures of carboxylic acid derivatives
Write the general mechanism of nucleophilic acyl substitution
Understand and apply the general reactivity of carboxylic acid derivatives
Write mechanisms of nucleophilic acyl substitution reactions to convert carboxylic acids into:
o acid chlorides
o anhydrides
o esters
o amides (with DCC)
o alcohols
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Problems during and after class: 16.6, 29, 30, 32, 37, 43, 51
 Lab Day 7 (2/24/10) - Experiment J Week 2 - Fischer Esterification
Day 13 (2/26/10)
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Read Ch. 16.3 - 16.5
Problems before class: 16.7 - 16.10, 16.12, 16.13
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Videos to watch in preparation for class: nucleophilic acyl substitution reactions, fischer
esterification
Write mechanisms of nucleophilic acyl substitution reactions to convert acid chlorides into:
o carboxylic acids
o amides
o anhydrides
o esters
Write the mechanism of the Fischer esterification
Write the mechanisms for both acid- and base-catalyzed ester hydrolysis
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Problems during and after class: 16.11, 14, 43, 44, 47
Day 14 (3/1/10) - Quiz #4
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Read Ch. 16.6, 16.7, 16.9, 16.10
Problems before class: 16.15 - 16.18, 16.21 - 16.24
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Videos to watch in preparation for class: polymers
Know the reactions for conversion of esters into:
o carboxylic acids
o amides
o alcohols, by reaction with both reducing agents and with Grignard reagents
Know the reactions for conversion of amides into
o carboxylic acids (hydrolysis)
o amines (reduction)
Describe structure and preparation of step-growth polymers such as polyamides (nylons) and polyesters
Analyze carboxylic acid derivatives using spectroscopy
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Problems during and after class: 16.19, 34, 40, 50, 57a&c, 58
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 Lab Day 8 (3/3/10) – No Lab This Week (Midterm Exam Prep)
Day 15 (3/5/10) - Midterm Exam (Chapters 13 - 16)
Carbonyl Alpha–Substitution and Condensation Reactions (Ch. 17)
Day 16 (3/15/10)
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Read Ch. 17.1 - 17.3
Problems before class: 17.1 - 17.4
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Videos to watch in preparation for class: keto-enol tautomerism; α-hydrogens; α-halogenation
Describe tautomers and how they differ from resonance structures
Write the mechanisms of both acid- and base-catalyzed keto-enol tautomerism
Write the general mechanism of a carbonyl α-substitution reaction, and apply it to specific reactions (such as
α-halogenation)
Use resonance to explain why some hydrogens are more acidic than others
 Problems during and after class: 17.27, 31, 32
 Lab Day 9 (3/17/10) - Experiment K Week 1 (Exp K Prelab Quiz) - Aldol Reaction
Day 17 (3/19/10)
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Read Ch. 17.3 - 17.4
Problems before class: 17.5, 17.6
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Videos to watch in preparation for class: malonic ester synthesis
Describe general acidity trends for organic molecules
Write the mechanism of enolate ion alkylation, and specifically apply it to write the mechanism of:
o Malonic ester synthesis
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Problems during and after class: 17.33, 60
Day 18 (3/22/10) - Quiz #5
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Read Ch. 17.4
Problems before class: 17.7, 17.9, 17.10
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Videos to watch in preparation for class: acetoacetic ester synthesis; direct alkylation
Write the mechanism of enolate ion alkylation, and specifically apply it to write the mechanism of:
o Acetoacetic ester synthesis
o Direct alkylation of ketones, esters and nitriles
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Problems during and after class: 17.8, 26, 34, 36
 Lab Day 10 (2/24/10) - Experiment L Week 1 (Exp L Prelab Quiz) - Multistep Synthesis
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Day 19 (3/26/10)
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Read Ch. 17.5 - 17.7
Problems before class: 17.11, 17.13 - 17.16
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Videos to watch in preparation for class: aldol reaction; aldol condensation; intramolecular aldol
reaction
Write the mechanisms of the following reactions:
o Aldol reaction
o Acid- and base-catalyzed aldol condensations
o Intramolecular aldol reactions
Discuss the different conditions used to perform carbonyl condensations versus α-substitutions
 Problems during and after class: 17.12, 17, 28, 30, 37, 39, 43
Day 20 (3/29/10)
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Read Ch. 17.8 - 17.10
Problems before class: 17.18 - 22
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Videos to watch in preparation for class: claisen condensation; dieckmann reaction; michael reaction
Write the mechanisms of the following reactions:
o Claisen condensation
o Dieckmann reaction
o Michael reaction - conjugate carbonyl addition
 Problems during and after class: 17,23, 29, 59, 65
 Lab Day 11 (3/31/10) - Experiment L Week 2 - Multistep Synthesis
Day 21 (4/2/10) - Quiz #6
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Read Ch. 17.11 - 17.12
Problems before class: 17.24, 17.25
Write the mechanism of the Claisen condensation between two thioesters in fatty-acid synthesis.
 Problems during and after class: 17.50, 17.55, 17.61
Amines And Heterocycles (Ch. 18)
Day 22 (4/5/10)
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Read Ch. 18.1 - 18.5
Problems before class: 18.1 - 18.6, 18.20, 26
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Videos to watch in preparation for class: naming amines
Write the names and draw the structures of amines
Describe the basicity of both aliphatic and aromatic amines, using electron density and resonance to explain
why some compounds are more basic than others
Describe the structure of amines at physiological pH
 Problems during and after class: 18.21, 23, 24, 25, 38
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 Lab Day 12 (4/9/10) - No lab this week
Day 23 (4/9/10)
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Read Ch. 18.6
Problems before class: 18.8, 18.10,
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Videos to watch in preparation for class: ways to make amines; complex amine synthesis; reductive
amination
Know the reactions for the synthesis of amines
o Reduction of nitriles, amides and nitro compounds
o SN2 reactions of alkyl halides (and the limitation of this synthetic method)
o Reductive amination of aldehydes and ketones
Write the mechanism of the reductive amination of a ketone to yield an amine
 Problems during and after class: 18.9, 33, 34, 40, 45
Day 24 (4/12/10) - Synthesis Exam Practice
 Lab Day 13 (4/14/10) - Synthesis Exam
Day 25 (4/16/10) - Quiz #7
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Read Ch. 18.7, 18.10
Problems before class: 18.11, 12, 13, 18,
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Videos to watch in preparation for class: hoffmann elimination; complex amine synthesis
Know the reactions of amines and heterocyclic amines:
o Alkylation and acylation
o Hoffmann elimination
o Electrophilic aromatic substitution
Analyze amines and heterocycles using spectroscopy
 Problems during and after class: 18.14, 27, 36, 41, 55
Biomolecules: Carbohydrates (Ch. 21)
Day 26 (4/19/010)
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Read Ch. 21.1 - 21.2
Problems before class: 21.1 - 21.5
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Videos to watch in preparation for class: fisher projection basics
Classify and describe the structural features of carbohydrates
Draw basic fisher projections
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Problems during and after class: 21.27, 28, 31
 Lab Day 14 (4/9/10) - Experiment N - Qualitative Organic Analysis
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Day 27 (4/23/09)
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Read Ch. 21.3 - 21.4
Problems before class: 21.6, 21.8 - 21.10
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Videos to watch in preparation for class: fisher projections sugars
Draw fisher projections of carbohydrates
Assign and use +/-, R/S and D/L nomenclature in carbohydrates
Describe the configuration of the aldoses; compare and contrast the D-aldoses
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Problems during and after class: 21.24, 21.26
Day 28 (4/26/10) - Quiz #8
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Read Ch 21.5
Problems before class: 21.11 - 21.15
Describe the structure, properties and functions of anomers (cyclic structures of monosaccharides), and write
the mechanism for their intramolecular formation from open-chain monosaccharides.
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Problems during and after class: 21.32, 33, 35, 37
 Lab Day 15 (4/28/10) - Lab Checkout
Day 29 (4/30/10) - Final Exam Review
Day 30 (5/3/10) - Final Exam Review
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