CHEM 2212 Lesson Objectives and Assigned Problems Plan, Fall 2008 (Dr. Pennington)
Lesson
Assignment
Questions
Before
class
1
 13.1 - 13.3
1, 2, 3-9
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,
41, 45, 53,
Know reactions to oxidize alcohols.
Write reactions for the preparation and reactions of thiols.
Name and draw structures of ethers and sulfides.
3
 13.6-13.11
14a-e, 16-19
13.L , 13.S
Write the mechanism of the Williamson ether synthesis.
Write reactions for the preparation and reactions of ethers.
29, 30, 39,
58, 59, 65, 66
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.
22d, 25, 28,
Know methods to oxidize aldehydes to carboxylic acids
30, 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, 9, 11,
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, 32, 33
34,
Write the mechanism of nucleophilic addition of alcohols to yield hemiacetals and acetals.
6
 14.9, 11
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
GGC - CHEM 2212 Lesson Objectives & Assigned Problems, Fall 2008; Pennington
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33, 41, 45, 47
Know the reactions of nitriles.
8
 15.7
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
9
 15.7 - 8
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.
GGC - CHEM 2212 Lesson Objectives & Assigned Problems, Fall 2008; Pennington
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
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.
Write the mechanism of alkylation of enolate ions and specifically apply it to write mechanisms for:
16
 17.4
7, 9, 10
b. acetoacetic ester synthesis.
26, 34, 36
c. direct alkylation of ketones, esters and nitriles.
Quiz #8
17
Midterm Exam (Chapters 13 thru 17.4)
Write the general mechanism of a carbonyl condensation reaction, and apply it to specific reactions.
18
 17.5 - 17.7
11, 12, 13,
14
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
29, 54, 59, 65
Write the mechanism of the intramolecular Claisen cyclization reaction, to yield a cyclic β-keto ester.
Write the mechanism of the Michael conjugate carbonyl addition reaction.
20
17.11 - 12
24, 25
Quiz #9
Write the mechanism of the Stork carbonyl condensation with enamines
50, 55, 61
Write the mechanism of Claisen condensation between two thioesters in fatty-acid synthesis.
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.
GGC - CHEM 2212 Lesson Objectives & Assigned Problems, Fall 2008; Pennington
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Know the reactions of amines and heterocyclic amines:
23
11, 12, 13,
 18.7 - 18.8 
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
GGC - CHEM 2212 Lesson Objectives & Assigned Problems, Fall 2008; Pennington
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