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CHEM 3104 Exam 1 Name:
This exam contains 100 points from 23 questions on 5 pages.
Circle the best response to each question below.
- (3 points) How many S'Q3 orbitals can an atom contain?
A. 1 B.. 2 C. 3 § 4 E. 5
- (3 points) Which OTle of the following compounds is the st rongest base?
~ .C H 3 B. NH; C. OH- (§ F
- (3 points) Which one of the following compounds contains a carbon-oxygen double
bond?
A. CH3C(OCH3hCH
B. CH
CH(OH)CH
C. CH
CH=CHCH
0H
~ CH3COCH
E. CH
0CH
- (3 points) 'Wh ich one of the following compounds contains an iso group?
A. (CH3)2CHCH2CH
B. (CH3)2NC H2CH
C. CH3CH2CII(CH3)CH2CH
D. CH
CH
CH
CH
E. CH
CH
COCH
- (3 points) Which Newman projection depicts two ethyl groups in a gauche arrangement?
H 3
C H 2
CC H 2
C H H 3
CH 2
CC H 3
H 2
CH 3 3
I H H H3^ C
H
H (^) CH 3
H CH 3
H (^) CH
~~C"'^3
CH 3 CH^
(^2) CH.\
CH 2
CH CH (^3) 3
/
- 6. (3 pOints) Which one of the following compounds has^ - the greatest amount of torsional
strain?
A. cyclo hept ene B. cyclohexane (^) c. cyclopentane 3 CYclOprOpa ne E. cycle
propene
Ie
Page 1 of 5 (^) out of 18
CHEM 3104 Exam 1
- (3 points) Which one of the following alkenes does not exist as a pair of geometric
isomers?
AI. 2-methyl-2-hexene
B. 2-methyl-3-hexene
C. 3-methyl-2-hexene
G3- methy 1-3- hexene
E. 5-methyl-2-hexene
- (3 points) A reaction with a negative free energy change means that the reaction is
A. endergonic @exergonic C. fast D. slow
- (3 points) Which reaction of alkenes utilizes a catalyst?
A. halogenation fs'\ hydration C. hydroboration D. hydrohalogenation
E. oxymercuration D
- (3 points) '\Thich one of the following reactions occurs without an intermediate? ..........,
A. halogenation B. hydration V hydroboration D hydrohalogenation
E. oxymercuration
Give the correct IUPAC name for each compound below, including designations
for stereoisomers where appropriate. , ~
(~3 C (Ill. C.;L. :)
I
s,.
- (5 points)
~
o~
1}. (5 points).
('(0 ht, ~V\
. J 4-f
ruf
"
I
cy __ 1 00
- I
~
l-"o J 0
2-
out of 27 Page 2 of 5
CHEM 3104 Exam 1
Give the best answer to each question below. Explain your reasoning where
appropriate.
- (5 points) Draw the most stable chair conformer oftrans-1-isobutyl-3-methylcyclohexane.
- (5 points) Arrange the following compounds in order of increasing boiling point: 1
hexanol, diisopropyl ether, 3,3-dimet 1-2-butanol, dipropyl ether, 3-hexanol.
CHEM 3104
23. (10 points) Draw the mechanism of : he reaction between 3-methyl-l-butene and C
Give the rUPAC name of the product.
Exam 1
.
2
Page 5 of 5 out of 10
