Download CHEM 2212 - Organic Chemistry II – Session B

CHEM 2212 - Organic Chemistry II
Lesson Objectives, Lesson Problems, Course Outline
Summer 2009 – Session B

Welcome to Team Tsoi!

Success in this class (and its lab) will occupy the vast majority of your time over the next 16 class days. Having all the material
concentrated into such a small amount of time will keep you from forgetting material from one week to the next. However, constant
studying and working problems is the key to your success here.

We will be focusing on working problems during class sessions, which means you HAVE TO BE PREPARED FOR CLASS
EVERY DAY. The semester is split up into separate lessons. There are preparatory assignments listed for each class – problems
you should have completed before attending that class. Also shown are the problems that we will plan to go through during
each class (these are usually more complex than the pre-class assigned questions), as well as problems to do after each class is
over.

You will be assessed by the in-class 12 quizzes during the semester (the lowest two may be dropped); the quiz schedule is listed in
the lesson planner and in the course schedule. There will also be a midterm exam and a cumulative final. A possible 50 instructor
points are also available to each of you – class participation, enthusiasm in the classroom, being an efficient worker in the lab,
effective preparation (for both class and lab) and a responsible attitude towards your own success are some of the things that will
earn instructor points.

Important note –there are days on which we have a quiz scheduled AND book problems to do for the new chapters after the quiz.
Sorry – 17 weeks of material in 16 days…
CHEM 2212 Lesson Objectives & Assigned Problems
1
CHEM 2211 / 2211L Overview – SUMMER 2009 – TEAM TSOI
Week
Date
Lesson
CHEM 2211
Quizzes
CHEM 2211 Lab
Week 1
25-Jun TH
1, 2
Ch 13
Quiz # 1
NO LAB
Week 2
29-Jun M
30-Jun TU
1-Jul W
2-Jul TH
3, 4
5, 6
7, 8
9, 10
Ch 13, 14
Chapter 14
Chapter 15
Chapter 15, 16
Quiz # 2
Quiz # 3
Quiz # 4
Quiz # 5
Experiment H
Experiment H
Experiment I
Prelab Quiz - Expt. I
Lab H Report due
6-Jul M
7-Jul TU
11, 12
13, 14
Quiz #6
Quiz # 7
Experiment I
Experiment J
Prelab Quiz - Expt. J
Lab I Report due
8-Jul W
9-Jul TH
15, 16
17
Chapter 16
Chapter 16, 17
Ch 17,
MIDTERM
EXAM
Chapter 17
MIDTERM
EXAM
No quiz
Experiment K
Prelab Quiz - Expt. K
13-Jul M
14-Jul TU
15-Jul W
16-Jul TH
18, 19
20, 21
22, 23
24, 25
Chapter 17
Chapter 17, 18
Chapter 18
Chapter 19
Quiz # 8
Quiz # 9
Quiz #10
Quiz # 11
20-Jul M
21-Jul TU
26, 27
28, 29
30
(review)
Chapter 21
Chapter 21, 23,
Quiz #12
Week 2
midpoint
Week 3
Week 4
22-Jul W
FINAL
EXAM (7/23)
CHEM 2212 Lesson Objectives & Assigned Problems
Prelabs
Prelab Quiz - Expt. H
Lab J Report due
Experiment K
Experiment L
Experiment L
Prelab Quiz - Expt. L
Synthesis
Review
Synthesis Exam
Review
Experiment N
FINAL
EXAM
Lab Reports
Lab K Report due
Lab L Report due
Prelab Quiz - Expt. N
Lab N Report Due
2
CHEM 2212 Lesson Planner – Team Tsoi
Lesson
Assignment
Questions
Before
class
1
 13.1 - 13.3
1-4, 6-9
Lesson Objectives Description
Questions During
and After class
Name and draw the structures of alcohols, phenols and thiols.
Describe trends in physical properties of alcohols, phenols and thiols.
20, 22, 23, 28,
Demonstrate how alcohols and phenols are both weakly acidic and weakly basic.
34, 35, 51, 70
Draw resonance structures to explain the higher acidity of phenols vs. alcohols.
Write reactions for the preparation of alcohols from carbonyl compounds
Write mechanisms for the acid-catalyzed dehydration of a 3 alcohol (E1), and the dehydration of 2 and 1 alcohols
with POCl3 in pyridine (E2).
2
 13.4 - 13.5
10, 11, 12
Quiz #1
Know reactions to convert alcohols into esters.
22, 31, 32, 33, 36,
45, 53
Know reactions to oxidize alcohols.
Write reactions for the preparation and reactions of thiols.
3
 13.6-13.11
13, 14, 16a-c
13.L , 13.S
17-19
Name and draw structures of ethers and sulfides.
29, 30, 39,
Write the mechanism of the Williamson ether synthesis.
58, 59, 65,
Write reactions for the preparation and reactions of ethers.
67, 69
Analyze alcohols, phenols and ethers using spectroscopy.
Name and draw structures of aldehydes and ketones.
4
 14.1 - 14.4
1, 2, 3, 4, 5
Know methods for the formation of aldehydes and ketones.
Know methods to oxidize aldehydes to carboxylic acids
22d, 25, 28,
38, 42
Write the general mechanisms for nucleophilic addition to aldehydes and ketones.
Quiz #2
List the common negatively charged nucleophiles and neutral nucleophiles.
Write the mechanism of acid and base-catalyzed hydration to aldehydes and ketones.
5
 14.5 - 14.8
6, 8, 10-12

Write the mechanism of nucleophilic addition via the Grignard reaction.
Write the mechanism of nucleophilic addition of amines to yield imines and enamines.
22a-c, 29, 30, 32, 33
34, 39
Write the mechanism of nucleophilic addition of alcohols to yield hemiacetals and acetals.
 14.9, 11,
6
13, 14, 17-19
Write the mechanism of nucleophilic addition of phosphorous ylides (Wittig Reaction).
Write the mechanism for the conjugate addition of a nucleophile to an β-unsaturated aldehyde or ketone.
14.12
14.L , 14.S
Analyze aldehydes and ketones using spectroscopy.
31, 44, 50, 54, 55,
60b-c
Quiz #3
Name and draw the structures of carboxylic acids and nitriles.
7
 15.1-6
1, 2, 3, 4, 5
7, 9
Explain the substituent effect on acidity.
14, 18, 21, 24, 25
Know reactions for preparation of carboxylic acids.
Know the general scheme of carboxylic acid reactions as outlined in Figure 15.2
CHEM 2212 Lesson Objectives & Assigned Problems
3
33, 41, 45, 47
Know the reactions of nitriles.
8
 15.7
9
 15.7 - 8
10, 11
26, 27, 32, 37,
Write the mechanism for base hydrolysis of a nitrile to yield an amide, and at higher temperatures, a carboxylic acid.
40, 43
Quiz #4
Write the mechanism for production of nitriles via the dehydration of an amide using thionyl chloride.
15.L , 15.S
12, 13
 16.1-16.3
1a-g, 2a-e,
Write the general mechanism for a nucleophilic acyl substitution reaction.
3, 4, 5, 6
Understand and apply the relative reactivity of carboxylic acid derivatives.
Analyze carboxylic acids and nitriles using spectroscopy.
49, 50, 51, 52, 53,
54
Name and draw structures of carboxylic acid derivatives.
10
29, 30, 32, 37, 51
Quiz #5
Know the nucleophilic acyl substitution reactions of carboxylic acids, for conversion into:
a. acid chlorides
11
 16.4 - 16.5
7, 8, 9, 11
12, 13
b. acid anhydrides
43, 44, 47, 50,
c. esters
d. amides
e. alcohols
Know the nucleophilic acyl substitution reactions of acid halides, for conversion into:
a. acids
b. anhydrides
c. esters
d. amides
Know the reactions of acid anhydrides.
Write the mechanism of Fischer esterification of a carboxylic acid to yield an ester.
Write the mechanisms of both base and acid-catalyzed ester hydrolysis.
12
 16.6, 16.7
16, 17
Know the reactions for conversion of esters into:
33, 34, 58,
a. carboxylic acids
Quiz #6
b. amides
c. alcohols via both reduction and Grignard reaction.
Know the reactions for conversion of amides into:
13
 16.7, 16.9
18, 19
16.10.
21, 22, 24
16.L, 16.S
a. carboxylic acids (hydrolysis)
40, 55, 56, 57
b. amines (reduction)
Describe step-growth polymers of polyamides (nylons) and polyesters, and understand their biological applications to
sutures and biodegradeable polymers.
Analyze carboxylic acid derivatives and their reactions using spectroscopy.
CHEM 2212 Lesson Objectives & Assigned Problems
4

14
 17.1-3
Write the mechanism of:
1, 2, 3, 4
a. acid-catalyzed keto-enol tautomerism
27, 31, 32,
b. base-catalyzed keto-enol tautomerism
Write the general mechanism of a carbonyl -substitution reaction, and apply it to specific reactions.
Quiz #7
Use resonance to illustrate why some hydrogens are more acidic than others.
Describe general acidity trends for organic molecules.
15
 17.4
5, 6
Write the mechanism of alkylation of enolate ions and specifically apply it to write mechanisms for:
33, 60
a. malonic ester synthesis.
16
Midterm Exam (Chapters 13 thru 17.4)
Write the mechanism of alkylation of enolate ions and specifically apply it to write mechanisms for:
17
 17.4
7, 9, 10
b. acetoacetic ester synthesis.
26, 34, 36
c. direct alkylation of ketones, esters and nitriles.
Write the general mechanism of a carbonyl condensation reaction, and apply it to specific reactions.
18
 17.5 - 17.7
11, 12-14
Quiz #8
17
a. aldol reaction
28, 30, 37, 39, 43,
b. acid and base catalyzed dehydration of β-hydroxy aldehydes and ketones.
c. intramolecular aldol reactions
Write the mechanism of the Claisen condensation reaction.
19
 17.8 - 10
18, 20-23
20
17.11 - 12
24, 25
29, 54, 59, 65
Write the mechanism of the Dieckmann reaction, to yield a cyclic β-keto ester.
Write the mechanism of the Michael conjugate carbonyl addition reaction.
Write the mechanism of the Claisen condensation between two thioesters in fatty-acid synthesis.
50, 55, 61
Quiz #9
Write the names and draw the structures of amines.
21
18.1 - 18.4
1,2,3 4-6
Describe the basicity of amines and arylamines, using elecrtron density and resonance to explain why some
compounds are more basic than others
24, 25, 30, 37
Describe structure of biological amines at physiological pH (Henderson-Hasselbalch equation)
Know the reactions for the synthesis of amines:
a. reduction of nitriles, amides and nitro compounds
Know the reactions for the synthesis of amines:
22
 18.5 - 18.6 
7, 8, 10
b. SN2 reactions of alkyl halides
33, 34, 40, 41, 45
c. reductive amination of aldehydes and ketones.
Quiz #10
Write the mechanism of reductive amination of a ketone to yield an amine.
CHEM 2212 Lesson Objectives & Assigned Problems
5
Know the reactions of amines and heterocyclic amines:
23
 18.7 - 18.8 
11, 12-14
18.10.
15
a. alkylation and acylation.
35, 36, 43, 44, 55
b. Hofmann elimination.
c. electrophilic aromatic substitution.
Analyze amines and heterocycles using spectroscopy.
Describe the structure and dipolar nature of amino acids in aqueous solution.
24
 19.1 - 4
1, 2, 3, 4, 5
7, 8
Quiz #11
Describe the 20 common amino acids shown in Table 19.1.
17, 19, 21, 29,
Write the reactions to synthesize amino acids:
a. amidomalonate synthesis
b. reductive amination.
Describe enzymes and apply them to generalized systems of enzymes, substrates and products.
25
19.9 - 10 
16
19.L, 19.S
Draw the energy diagram of uncatalyzed vs. catalyzed processes.
45, 52
Describe how enzymes work.
Write the mechanism of the addition of acetyl CoA to oxoloacetate to give (S)-citryl CoA, catalyzed by citrate synthase.
26
 21.1 - 2
1, 2-5
Quiz #12
Classify and describe the structural features of carbohydrates.
27, 28, 31
Draw basic Fischer projections
Draw Fischer projections of carbohydrates.
27
21.3 - 4
6, 8, 9, 10
Assign and use +/-, R/S and D/L nomenclature in carbohydrates.
24, 26
Describe the configuration of the aldoses and compare and contrast the D-aldoses.
28
 21.5
11, 12 - 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.
32, 33, 35, 37
Quiz #13

29
23.1 - 4
Describe the structures, properties and functions of lipids:
23.1-4, 13,
14
a. waxes
23.9
b. fats
23.L, 23.S
c. oils.

16, 21, 24, 26, 39,
40, 48
d. phospholipids.
Describe the structures of steroids.
30
Final Exam Review
CHEM 2212 Lesson Objectives & Assigned Problems
6