Practice Questions for 32-235 Exam 1

Note these are for reviews only. Make sure that you can do all homework without
consulting the Solutions Manual and that you can complete them in a reasonable
amount of time (speed of essence).

Multiple Choices (Choose only ONE answer !)

1. What kind of molecular orbital results when the two atomic orbitals shown below
interact in the manner indicated?

(a) * (b) (c)* (d) (e) none of the above

2. Which of the following matches of names and molecules are correct ?

A. Alcohol I. HCOOH
B. Aldehyde II. (CH3)3COH
C. Ketone III. CH3OCH3
D. Acid IV. CH3COCH3

(a) C and III, D and IV (b) A and II, C and IV

(c) A and III, B and IV (d) B and II, D and I
(e) none of the above

3. The number of bonds in the molecule shown below is

CH3CH=CHCH2C CH
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5

4. The relationship of the following two structures is

H3C Br Br Br
C C C C
Br CH3 H3C CH3

(a) structural isomers (b) geometric isomers (c) the same

(d) not isomeric (e) conformational isomers
5. Which are the correct orbital hybridizations for the carbon atoms in the following
structures ?

+
CH3CH3 CH2=CH2 CH3 HC N H2O
sp3 sp2 sp2 sp2 sp

III IV V
I II

(a) I, II, III (b) I, II, IV (c) II, III, V (d) III, IV, V
(e) I, III, V

6. Which of the following compounds is nonpolar (dipole moment = 0) ?

Cl Cl
H2O NH3 CH3Cl C C
H H
(a) (b) (c) (d)

(e) none of the above

7. Which compound would have the lowest boiling point ?
OH

OH
O
(a) (b) (c)

CH2OH

OH

(d) (e)
8. Consider the three isomeric alkanes n-hexane, 2,3-dimethylbutane, and 2-
methylpentane. Which of the following correctly lists these compounds in order
of increasing boiling point?

a) 2,3-dimethylbutane < 2-methylpentane < n-hexane

b) 2-methylpentane < n-hexane < 2,3-dimethylbutane
c) 2-methylpentane < 2,3-dimethylbutane < n-hexane
d) n-hexane < 2-methylpentane < 2,3-dimethylbutane
d) n-hexane < 2,3-dimethylbutane < 2-methylpentane

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9. How many tertiary hydrogens are there in the following structure:

(a) 1 (b) 2 (c) 3 (d) 4 (e) 5

10. Which of the following pairs of formula represent structural isomers ?

F
(a) and F

F HH F F
(b) F and F
H F H HH

(c) CH3CH2CH2NH2 and (CH3)3N

d) More than one of these
e) None of these

11. Which of the following is a representation of the gauche conformer of butane.

CH3 CH3 H3C CH3 HH

H H H3C H

H H H H H H3C HCH3
H H H
H
CH3 H

(a) (b) (c) (d)

(e) none of the above

12. Which of the above conformations is the least stable ?

(a) (b) (c) (d) (e)

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13. Which drawing represents the most stable conformation of cis-1-tert-butyl-4-
methylcyclohexane.

CH3 CH3
CH3 C(CH3)3 CH3
C(CH3)3

C(CH3)3 C(CH3)3
(c) (d)
(a) (b)

(e) none of the above

14. If stronger bonds are broken and weaker bonds are formed, then the reaction is

(a) is exothermic (b) is endothermic (c) has a positive S

(d) has a negative S (e) is spontaneous

15. Which of the following molecules can exist as geometric isomers?

CH3 H
(A) (B) CH2 C (C) CHCH2CH3
CH3 Cl

(D) CH3CH2CHCH3 (E) CH3CH CHCH3

Cl
16. The relationship between the following two structures is
H H H CH3
H C CH2 C H CH3CH2 C CH2 C H
CH2CH3 CH3 H H
(A) same (B) constitutional isomers (C) geometric isomers
(D) not isomers (E) structural isomers

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17. Which is an acceptable resonance structure for the following drawing?
H
C O
H CH3

(A) CH3CH OH (B) CH2 O CH3 (C) CH3CH2O

(D) CH3CH OH (E) None of the above

18. The relationship of the following two structures is

H3C CH3 H CH3

H H H3C H

(A) structural isomers (B) conformational isomers (C) the same

(D) not isomeric (E) stereoisomers

19. Which is(are) the correct orbital hybridization(s) for the C and N atoms in the
following structures ?
CH3CH3 CH2=CH2 NH3 HC CH
sp3 sp sp2 sp2
I II III IV

(A) I (B) II, III (C) III, IV (D) I, III (E) II

20. The b.p. of the following compounds is expected to decrease in this order
(highest b.p. first):
CH3CH2CH2CH3 CH3CH2CH2CH2CH3
I II

CH3CH2CHCH3 CH3CH2CH2CH2OH
CH3
III IV
(A) II > III > IV > I (B) III > I > II > IV (C) III > II > IV > I
(D) IV > II > III > I (E) I > II > III > IV

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21. An acceptable name for the following structure is

(A) 8-t-Butyl-4-ethyl-3-methyldecane (B) 3-sec-Butyl-7-tert-butylnonane

(C) 3,7-Diethyl-2,2,8-trimethyldecane (D) 4,8-Diethyl-3,9,9-trimethyldecane
(E) none of the above

22. Which statement is true regarding the following conformations for butane?
H CH3
H H HH HH H H

CH3 H H H
CH3 H3CCH3 CH3

I II III
(A) I is less stable than II because of steric strain
(B) III is less stable than I due to its torsional strain
(C) III is called gauche conformation
(D) The steric strain in II is greater than in I
(E) III has more energy than II

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23. Which of the following molecules is the least stable ?
CH3

H H H3C H H
H
CH3 CH3 H CH3 CH3
(A) (B) (C)

H CH3 H3C CH3

CH3 H H H

(D) (E)

24. Which name(s) is(are) acceptable for the following compound?

Cl CH3

(A) 5-chloro-2-methylcyclohexane
(B) 4-chloro-2-methylcyclohexane
(C) 1-chloro-3-methylcyclohexane
(D) 2-chloro-5-methylcyclohexane
(E) More than one of these

25. Which of the following represents the most stable conformation of cis-1-
isopropyl-4-methylcyclohexane?

CH(CH3)2 H

H CH(CH3)2
H H3C

CH3 H
(A) (B)
CH(CH3)2
H
H
CH(CH3)2 H3C
H
H
CH3
(C) (D)

(E) None of these fits the name given

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26. How many tertiary hydrogen(s) are(is) there in the following structure?

(A) 1 (B) 2 (C) 3 (D) 6 (E) 10

27. The strength of the following bases decreases in the order of (strongest first):
O
CH3O CH3 NH2 CH3C O
I II III IV
(A) I > IV > III > II (B) III > IV > I > II (C) II > I > III > IV
(D) IV > I > II > III (E) II > III > I > IV

28. Which molecule is expected to have the largest molecular dipole moment ?
H Cl
BH3 CH3Cl
Cl H
(B) (C)
(A)

CCl4 F C C F
(D) (E)

29. The formal charge on nitrogen in the Lewis structure below is

H H H
H C C N
H
H
(A) +2 (B) +1 (C) 0 (D) -1 (E) -2

30. Considering the following acid-base reaction, which statement is NOT true?
O O
+
CH3 C O H + NH3 CH3 C O + NH4

I II III IV
pKa = 4.7 pKa=9.2
(A) I is more acidic than IV
(B) II is more basic than III
(C) The equilibrium favors the right
(D) The two C-O bonds in III are of different length.
(E) more than one of the above

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31. When the 1s orbitals of two hydrogen atoms combine to form a hydrogen
molecule, how many molecular orbitals are formed ?

(A) one (B) two (C) three (D) four (E) five

32. The nitrogen atom in the molecule below is sp 2 hybridized. What is the
geometry of the atoms connected to nitrogen ?

CH2 NH2
(A) square (B) tetrahedral (C) trigonal planar
(D) linear (E) pyramidal

33. Which of the following is the best description for the C=N bond above?

(A) It results from sp2(C)-sp2(N) overlap

(B) It results from sp3(C)-sp2(N) overlap
(C) The two bonds are of same property
(D) One bond is from sp2(C)-sp2(N) and the other from 2 p orbitals
(E) None of the above

34. The relationship of the following two molecules is best described by

CH3 CH3

(A) structural isomers (B) geometric isomers

(C) not isomers (D) homologous
(E) conformational isomers

35. Which of the following bonds can act to form hydrogen bonding

(A) O-H (B) N-H (C) C-H (D) C-C

(E) more than one the above

36. The boiling point of straight chain alkanes increases as the number of carbons
increases. This is because

(A) the larger the molecule, the greater the dipole moment
(B) Larger molecules usually can form hydrogen bonding better
(C) Larger molecules can pack tightly together
(D) Larger molecules have greater surface therefore stronger London Forces
among them.
(E) None of the above

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Essay Questions

1. Use the curved arrow formalism(electron pushing) to indicate the movement of

electron pairs in the following reaction. Indicate in the boxes which reactants
are nucleophile (Nu) and/or electrophile (E).

CH3CH2O + CH3 I CH3CH2OCH3 + I

2. Draw the important resonance contributing forms for the structure shown below.
(Use electron arrow pushing for help)

3. Give an acceptable IUPAC name for the following compound:

4. (A) Write the two chair conformations for cis-1-tert-butyl-2-ethylcyclohexane (the following
two templates are drawn to help you)

A B

(B) In the above conformations, label the positions occupied by tert-butyl and ethyl groups by
using "ax" for axial and "eq" for equatorial positions.
(C) Determine which conformation would have a higher energy and briefly explain the reason.
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5. The three compounds below have identical or nearly identical molecular mass. Rank them in
the increasing order (lowest first) of their boiling points, and briefly explain your reasoning.

CH3CH2CH2CH2OH CH3CH2OCH2CH3 HOCH2CH2OH

A B C
6. Draw the Lewis structures for three compounds with a formula of C3H8O. What is the
relationship among these three compounds?

7. Redraw each molecule below to show lone pair electrons, then arrange them in the order of
increasing basicity (lowest first, use <). Explain your reasoning for the order.
O
CH3CH2O CH3CH2NH CH3C O
A B C

8. Draw the important resonance structures for the following molecule. (hint: try electron arrow
pushing)
O
H C CH CH CH2

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