Previous Quiz/Exam Keys
CHM 2430 - Survey of Organic Chemistry
*Be sure to read the note at the bottom of this page!*

[Don't forget to check out the Organic Chemistry Reaction Drills for additional help!]
Quiz/Exam
Chapter(s)
Topics
Quiz 1
a b c
d e f
1 bond angles/lengths, hybridization, Lewis structures
Quiz 2
a b c
d e f
2 alkane names, cyclohexane chair conformations, axial/equatorial positions, Newman projections
Quiz 3
a b c
d
e
 f
3
alkene names, E/Z alkene geometry, nature of multiple bonds, alkane oxidation (combustion) and free-radical halogenation (3°>2°>1° selectivity)
Exam I
A
B
 C
D
 E
 F
1-3
Lewis structures, bond angles, hybridization, isoprene rule, cyclohexane conformations, Newman projections, alkane/alkene nomenclature
Quiz 4
a
 b
 c
d
 e
 f
 3-4 cis/trans geometry, reaction energy diagrams (Eact, DH, transition state, etc.)
Quiz 5
a
 b
 c
d
 e
 f
 4
R/S configuration, carbocations (3o>2o>1o stability), alkene reduction (H2/catalyst; to cis alkane) and oxidation (KMnO4, cold; to cis diol)
Quiz 6
a
 b
 c
d
 e
 f
 4-5
optical activity/rotation, chiral centers, enantiomers, diastereomers, Fischer projections, R/S configuration, dextro- vs. levorotatory
Quiz 7
a
 b
 c
d
 e
 f
 5-6
R/S configuration, acidity/basicity, Bronsted-Lowry vs. Lewis acids, conjugate bases/acids, pKa (lower means stronger acid)
Exam II
A
 B
 C
D
 E
 F
4-6
alkene names, R/S configuration, racemization, carbocation stability (3o>2o>1o), reaction diagrams (exo- vs. endothermic, trans. state vs. reactive intermed., Eact, DH), alkene electrophilic additions (Br2, cold KMnO4 , H3O+, H2/cat., HX), Lewis acids/bases, pKa
Quiz 8
a
 b
 c
d
 e
 f
7 alcohol/ether names, SN1 vs. SN2 reactions, alcohol oxidation (PCC, H2CrO4)
Quiz 9
a
 b
 c
d
 e
 f
8  halide names, SN1 vs. SN2 , effect of protic vs. aprotic solvents, nucleophiles, leaving groups
Quiz 10
a
 b
 c
d
 e
 f
9
aromatics, ortho/meta/para positions, electrophilic aromatic substitution (halogenation, nitration, Friedel-Crafts alkylation/acylation), NO2 reduction to NH2
Exam III
A
 B
 C
D
 E
 F
7-9
nomenclature (alcohols/halies/aromatics), alcohol oxidation (PCC, H2CrO4)/elimination, EAS (o,m,p directors), SN1/SN2/E1/E2 (incl. mechanisms), synthesis (WORK BACKWARDS), acidity (stability of conjugate bases), aromaticity (criteria)
Extra Quiz
ab 		7-9 see topic list for Exam III
Quiz 12
a
 b
 c
d
 e
 f
11
aldehyde/ketone nomenclature, synthesis of carbonyls, Grignard reagents - rxn. with formaldehyde, aldehydes, ketones, CO2, ethylene oxide - carbonyl reaction with H2O, ROH
Quiz 13
a
 b
 c
d
 e
 f
11-12
amines (alkyl and aromatic), prepn. by nitration then reduction, diazonium salts (conversion to halides, CN, OH, H), aldehyde/ketone nomenclature, synthesis of carbonyls, Grignard reagents, rxn. with formaldehyde, aldehydes, ketones, CO2, ethylene oxide
Exam IV
A
 B
 C
D
 E
 **
10-12
amines (alkyl and aromatic), prepn. by nitration then reduction, diazonium salts (conversion to halides, CN, OH, H), aldehyde/ketone nomenclature, synthesis of carbonyls, Grignard reagents, rxn. with formaldehyde, aldehydes, ketones, CO2, ethylene oxide; carboxylic acids, acidity (effect of substituents), reduction, esterification, acid chlorides, decarboxylation 
Quiz 14
a
 b
 c
d
 e
 f
14
acid chlorides/anhydrides, esters, amides; relative reactivity toward nucleophiles; reaction with water, alcohols, ammonia/amines; leaving groups incl. relationship to basicity
Quiz 15
a
 b
 c
d
 e
 f
15 enolate anions, stabilization by resonance; acidity of α-hydrogens; nucleophilicity of enolates; aldol condensation (aldehydes/ketones) to β-hydroxy carbonyls, dehyration to α,β-unsaturated carbonyls; Claisen condensation (esters) to β-keto esters; intramolecular aldol/Claisen to ring compounds
Quiz 16
a
 b
 c
d
 e
 f
20
enolate anions, resonance contributors, ester enolates, Claisen condensation (incl. mixed), ester saponification (basic hydrolysis) followed by thermal decarboxylation for β-keto esters (one-step reaction possible)
NOTE: Since the pace of each semester varies, and especially since this course was recently reduced from meeting 4x/week to 3x/week (meaning only three exams instead of four), the quizzes/exams above may not correspond exactly to the material our quizzes/exams do.  It's best to check the topics against the material you know you're responsible for on any quiz or (especially) exam.
** Another unfortunate consequence of reducing the number of lectures from four to three per week is that we have less time for exams, so there will be, from now on, no Exam IV, unless the timing of the class works out that we can spare the extra hour.  Another option is to have it in an evening, because I personally think you deserve four exams so that no single exam covers too much.  I'll talk to the class about this on the first class day.  Even if we can't have a 4th exam, the old ones are still great study guides.

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