CHEM 31 NON-DEPARTMENTAL EXAM

,;it.JL11PLE CHOICE: Write the CAPITAL LETTER of the best answer.

_1. \Vhich molecule has the largest dipole moment?
\A) HCl
(B; CCl4
(C)
(D)
___ 2. Which of the following substances is achiral?
3. VVhich of the following structures is the MOST
stable conformation of cis-1,3-dimethylcyclohexane?
_ 4. Which of the following physical properties differ
for each of a pair of enantiomers?
(A) Solubility in ethanol
(B) Direction of plane-polarized light
(C) Boiling point and melting point
(D) Index of refraction
_5. What type of isomerism exists between the ketones
shown above?
(A) position
(B) configurational
(C) confonnationai
(D) geometric
(E) optical
_6. Which of the following is NOT an isomer of
CsHc?
(A) Cyclohexane
(B) Methylcyclopropane
(C) 1,1,2-trimcthylcyclopropane
(D) trans-1,2-d.imethylcyclobutane
(E) Ethylcyclobntanc
__ 7. Which of the foiiowiug is the correct order of
INCREASING tmderlined C- C bond length:
(I) - H=CH2 (11) CH3.H1 - H2TH3
(III) CH3- = -- CH3 (IV) CH3.H=Qf - CH
3
(A) I < li <III < IV
(B) IV < III < II < I
(C) II < I < IV< lli
(D) III < IV < I < II
(E) III < IV < II < I
8. Determine the relationship between the two
molecules:
(A) constitutional isomers
(B) enantiomcrs
(C) d.iasteriomers
(D) identical molecules
_9. What is the correcl name for lltis molecule?
H3C\.--l
H''/ ,CI
Br CH
3
(A) (2RJR)-2-bromo-3-chlorobutane
(B) (2S.3R)-2-bromo-3-chlorobutane
(C) (28,35)-2-bromo-3-chlorobutane
(D) (2R.3S)-2-bromo-3-chlorobulane
_10. Detennine the double bond stereochemistry (E or
Z) for the following molecules:
(A)
(B)
I: ; II: E
l: Z; II: Z
I
F>=<Br
H I
II
(C)
(D)
I: E: TI: Z
1: Z; II: E
_11. Which of the following compounds would yield
tltis energy-rotation diagram?

Degrees ofRotat1a1
(A)

.. c-c
H'''j \
(C) H Br
B\ _,H
.. c- c-H
H'' J \
(D) H Br
U. The most stable conformational isomer of cis-l-
,jf01110-2-chlorocyclohexane will have _ _ _
.,AI both halide atoms in axial positions
=5) both halide atoms in equatorial positions
, C! the bromine atom in an position and the chlorine
Mom in an equatorial position
::D) the bromine atom in an equatorial position and the
;-:hlmine atom in an axial position
13. Which compound has the HIGHEST boiling
_;:Klint?
n-decane
Jj) 2.2.3.3-tetramethylbutane
7..,2,3-trimethylpentane
J)) 4-methyi.nonane
_14. Which of the following acid derivatives has the
LOWEST melting point?
:A) CH
3
COCJ
(B) CH
3
COBr
(C) CH3CONH2
(D)CH3COOH
_15. Vv'hat is the percentage composition of a mixture
of 2 enantiomers whose observed rotation is -9.0, and the
specific rotation of a pure enantiomer is -12?
(A) 75% (+) enantiomer, 25% (-) enantiomer
(B) 25% (+) enantiomcr, 75% (-) enantiomer
(C) 87.5% (+) enantiomer, 12.5% (-) enantiomer
(D) 12.5% (+) enantiomer. 87.5% (-) enantiomer
16. Which is the correct order of INCREASING bond
angle?
..

I< II <III
(B) IIi < IT < I
I
(C) II <I<ill
(D) II< ITI <I
n. Which is the correct order of DECREASING
bond length'?
(A) H3C-CH3 > H3C-NH2 > H3C-OH
(B) H
3
C-OH > H3C-NH2 > H3C--CH3
(C) H
3
C-CH
3
> H
3
C-OH > H3C-NH2
(D) H3C-NH2 > H3C-CH3 > H3C-OH
18. Which compound has the 1-llGHEST melting

(A) benzene (C) benzoic acid
(B) benzaldehyde (D) sodium benzoate
19. Which of the following cyclohexane
conformations is the LEAST stable?
(A) chair (C) boat
(B) half-chair (D) twist boat
_20. What is a proper name for the following ester?
(A) 2-butyl ethylester
(B) ethyl 2-pentanoate

(C) ethyl 2-methylbutanoate
(D) methylbutanoic ethyl ester
_21. Which of the following compounds is optically
active?
A_
(A) \_/ (C) H3C" v-cH3
(B)

U (D) All of these.
22. Which functional group is NOT present in
Norethindrone, a synthetic derivative of progesterone?
(A) ketone
(B) alkene
0

1_"""1-">--c=cH

(C) alcohol
(D) ether
_23. Which of the following statements is TRUE for
the pair of compounds shown below?

(A) They are positional isomers.
(B) 1-hexene has a lower melting point than cyclohexane.
(C) 1-hexene has a higher boiling point than cyclohexan.e.
(D) They are chain isomers.
_24. How many possible stereoisomers are there in the
compound shown below?
'b)
(A)2 (B) 4 (C) 16 (D)32
25. Which of the following statements BEST explains
why ethyl amine has a higher boiling point than dimethyl
amine?
(A) Ethyl amine is less symmetrical compared lo
dimethyl amine.
(B) Ethyl amine is more branched than dimethyl amine.
(C) Ethyl amine has a higher molecular weight than
dintethyl amine.
(D) Ethyl amine can have more hydrogen bonds than
dimethyl amine.
PROBLEM-SOLVING: Write your answers neatly at the
back of this test paper.
1. Using the Newman projection, draw the staggered
conformations of 2,3-dimetbylbutane in order of
increasing energy.
2. Draw the geometric isomers of 1,3,5-
trimethylcyclohexane and indicate the positions (cis or
trans) of the substituents relative to tlte methyl group at
Cl.