CHEM 202 Chemistry Molecules Worksheet

SUMMER 2022NAME:
CHEM 202
FINAL EXAM
DATE:
Draw structures corresponding to the names given.
1.
m-fluoronitrobenzene
2.
p-bromoaniline
3.
o-chlorophenol
4.
3,5-dimethylbenzoic acid
5.
1-phenyl-3-methylpentane
For each molecule below, predict whether the molecule would be expected to show aromatic character or not.
Explain your answer in each case.
O
6.
N
H
OH
7.
+
O
8.
N
MATCH a structure or term from the following list with each description below. Place the letter of the structure
or term in the blank to the left of the description.
a.
b.
benzyne
+
NO2
c.
d.
e.
f.
g.
h.
R 3C+
electron-donating
+
NO
Meisenheimer complex
R − C ≡ O+
electron-withdrawing
9.
The reactive electrophile in Friedel-Crafts acylation reactions.
10.
The electrophile in aromatic nitration.
11.
Groups which activate aromatic rings towards electrophilic substitution.
12.
Groups which activate aromatic rings towards nucleophilic substitution.
13.
Intermediate in the elimination-addition mechanism of nucleophilic aromatic substitution.
Give the major organic product(s) of each of the following reactions. If none is predicted, write “N.R.”
CH3CH2CH2Cl
14.
AlCl3
OCH3
15.
NO2
Br2
FeBr3
O
16.
H3C
NHCCH3
Cl2
FeCl3
CH3
17.
SO3
H2SO4
18.
Br
I2
CuCl2
CH3
19.
1 equiv. Cl2
FeCl3
O
20.
CH3CCl
CH3O
AlCl3
Choose the best reagent(s) from the list provided below for carrying out the following conversions. Place the
letter of the reagent in the box beside the reaction number over the arrow. There is only one answer for each
reaction.
a.
b.
c.
d.
e.
f.
g.
h.
i.
KMnO4 , H 3O +
Br2 , FeBr3
Cl2 , FeCl3
CH 3Cl, AlCl3
HNO3 , H 2SO4
ClCO(CH2)2CH3, AlCl3
CH3CH2CH2CH2Cl, AlCl3
H 2 Pd
NBS, peroxides
Br
1.
21.
2.
NO2
O
22.
1.
2.
NO2
23.
Cl
1.
2.
3.
CO2H
Br
24.
1.
2.
3.
CHCH2CH2CH3
Consider the reaction below to answer the following questions.
O
O
+
HOCH2CH2OH
A
B
O
HCl
C
+
H2O
D
25. The nucleophile in this reaction is:
26. The catalyst in this reaction is:
27. The product of this reaction is called:
Give the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant
stereochemistry.
CH2OH
28.
PCC
CH2Cl2
29.
O
CH3(CH2)10COCH3
1. DIBAH, toluene
2. H3O+
1. O3
30.
2. Zn, H3O+
O
31. H3C
C
CH
CH2
+ HN(CH2CH3)2
ethanol
O
32.
HOCH2CH2CH2OH
HCl
Br
O
33.
H3C
C
MgBr
+
H
1. ether
2. H3O+
Choose the BEST reagent for carrying out each of the following conversions.
O
O
A. LiAlH4, THF
C. 1. DIBAH, toluene
2. H3O+
B. NaBH4, ethanol
D. All of the above work well
O
O
35.
A. 1. PhMgBr, ether
2. H3O+
C. (C6H5)3P=CHC6H5, THF
36.
H
OCH3
34.
B. 1. PhCH2MgBr, ether
2. H3O+
D. Li(C6H5)2Cu, ether
O
A. 1. PhMgBr, ether
2. H3O+
C. (C6H5)3P=CHC6H5, THF
B. 1. PhCH2MgBr, ether
2. H3O+
D. Li(C6H5)2Cu, ether
O
C
37.
CH2OH
H
A. NaBH4, ethanol
C. NaOH, H2O
B. CH2PPh3
D. All of the above
Propose structure(s) for the starting material(s), reagent(s), or major organic product(s) of the following reactions
or sequences of reactions. Show all relevant stereochemistry.
38.
HBr, H2O
CH3
O
39.
CH2
1. Hg(O2CCF3)2, (CH3)3COH
2. NaBH4
O
40.
m-chloroperoxybenzoic acid
CH2Cl2, rt
CH3
41. H3C
C
H
C
H
Cl2
H2O
NaOH
H2O
C
H3CH2C
H3C
C
H
CH3
CH3
42.
O
43.
H
H2O
NaNH2
NH3
S
Br
1. H2NCNH2
2. NaOH, H2O
44.
S
CH3
H2O2, H2O
rt
45.
OH
O
ether
I