Spring 2010 – CHEM 2212Organic Chemistry II –Daily Lesson Objectives
Alcohols, Phenols and Thiols;Ethers and Sulfides (Ch. 13)
Day 1 (1/11/10) – Introductionto CHEM 2212 / Start of Chapter 13
Read Ch. 13.1 - 13.2
Problems before class: 13.1 - 5
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
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)
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)
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)
Read Ch. 13.4 - 13.7
Problems before class: 13.11 -14, 24f-I, 58
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
Problems during and after class: 13.22, 31, 33, 36, 59
Day 4 (1/25/10) - Quiz #1
Read Ch.13.8 -13.9, 13.11
Problems before class: 13.15 - 19, 65
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
Problems during and after class:13.29, 30, 39, 41, 48, 66, 69
Lab Day 3 (1/27/10) - Experiment H Week2 - Oxidation of 4-chlorobenzyl alcohol
Aldehydes and Ketones; Nucleophilic Addition Reactions (Ch. 14)
Day 5 (1/29/10)
Read Ch. 14.1 - 14.4
Problems before class: 14.1 - 5, 25a-e
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
Problems during and after class: 14.22d, 25f-j, 26, 27, 30, 38, 42
Day 6 (2/1/10)
Read Ch. 14.5 - 14.6, 14.9
Problems before class: 14.6, 14.7, 14.13, 14.29
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)
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)
Read Ch. 14.7 - 14.8
Problems before class: 14.8, 14.10, 14.12
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
Problems during and after class:14.9, 22a-c, 24, 34,40
Day 8 (2/8/10) - Quiz #2
Read Ch. 14.9, 14.11, 14.12
Problems before class: 14.16, 14.17, 14.21, 14.60c
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
Problems during and after class: 14.54, 55, 56, 57, 60b,
Lab Day 5 (2/10/10) - Experiment I Week 2 - Wittig Reaction
Carboxylic Acids and Nitriles (Ch. 15)
Day 9 (2/12/10)
Read Ch. 15.1 - 15.2, 15.4 - 15.5
Problems before class: 15.1, 2, 3, 6, 7, 9, 32
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
Problems during and after class: 15.14, 18, 21, 24, 33, 45
Day 10 (2/15/10)
Read Ch. 15.6 - 15.7
Problems before class: 15.11, 26, 27
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
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
Read Ch. 15.7 - 15.8
Problems before class: 15.12, 15.13, 53
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
Problems during and after class: 15.38, 43, 51, 52
Carboxylic Acids Derivatives: Nucleophilic Acyl Substitution Reactions (Ch. 16)
Day 12 (2/22/10)
Read Ch. 16.1 -16.2
Problems before class: 16.1a-g, 16.2a-g, 16.3 - 16.5
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:
- acid chlorides
- anhydrides
- esters
- amides (with DCC)
- alcohols
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)
Read Ch. 16.3 -16.5
Problems before class: 16.7 - 16.10, 16.12, 16.13
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:
- carboxylic acids
- amides
- anhydrides
- esters
- Write the mechanism of the Fischer esterification
- Write the mechanisms for both acid- and base-catalyzed ester hydrolysis
Problems during and after class:16.11, 14, 43, 44, 47
Day 14 (3/1/10) - Quiz #4
Read Ch. 16.6, 16.7, 16.9, 16.10
Problems before class:16.15 - 16.18, 16.21 - 16.24
Videos to watch in preparation for class:polymers
- Know the reactions for conversion of esters into:
- carboxylic acids
- amides
- alcohols, by reaction with both reducing agents and with Grignard reagents
- Know the reactions for conversion of amides into
- carboxylic acids (hydrolysis)
- amines (reduction)
- Describe structure and preparation of step-growth polymers such as polyamides (nylons) and polyesters
- Analyze carboxylic acid derivatives using spectroscopy
Problems during and after class:16.19, 34, 40, 50, 57a&c, 58
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)
Read Ch. 17.1 - 17.3
Problems beforeclass: 17.1 - 17.4
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)
Read Ch. 17.3 - 17.4
Problems beforeclass: 17.5, 17.6
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:
- Malonic ester synthesis
Problems during and after class: 17.33, 60
Day 18 (3/22/10) - Quiz #5
Read Ch. 17.4
Problems before class: 17.7, 17.9, 17.10
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:
- Acetoacetic ester synthesis
- Direct alkylation of ketones, esters and nitriles
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
Day 19 (3/26/10)
Read Ch. 17.5 - 17.7
Problems before class: 17.11, 17.13 - 17.16
Videos to watch in preparation for class:aldol reaction; aldol condensation; intramolecular aldol reaction
- Write the mechanisms of the following reactions:
- Aldol reaction
- Acid- and base-catalyzed aldol condensations
- 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)
Read Ch. 17.8 - 17.10
Problems before class: 17.18 - 22
Videos to watch in preparation for class:claisen condensation; dieckmann reaction; michael reaction
- Write the mechanisms of the following reactions:
- Claisen condensation
- Dieckmann reaction
- 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
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)
Read Ch. 18.1 - 18.5
Problems before class: 18.1 - 18.6, 18.20, 26
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
Lab Day 12 (4/9/10) -No lab this week
Day 23 (4/9/10)
Read Ch. 18.6
Problems before class: 18.8, 18.10,
Videos to watch in preparation for class:ways to make amines; complex amine synthesis; reductive amination
- Know the reactions for the synthesis of amines
- Reduction of nitriles, amides and nitro compounds
- SN2 reactions of alkyl halides (and the limitation of this synthetic method)
- 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
Read Ch. 18.7, 18.10
Problems before class: 18.11, 12, 13, 18,
Videos to watch in preparation for class:hoffmann elimination; complex amine synthesis
- Know the reactions of amines and heterocyclic amines:
- Alkylation and acylation
- Hoffmann elimination
- 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)
Read Ch. 21.1 - 21.2
Problems before class: 21.1 - 21.5
Videos to watch in preparation for class:fisher projection basics
- Classify and describe the structural features of carbohydrates
- Draw basic fisher projections
Problems during and after class: 21.27, 28, 31
Lab Day 14 (4/9/10) -Experiment N - Qualitative Organic Analysis
Day 27 (4/23/09)
Read Ch. 21.3 - 21.4
Problems before class: 21.6, 21.8 - 21.10
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
Problems during and after class: 21.24, 21.26
Day 28 (4/26/10) - Quiz #8
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.
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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