CH 331/1st Midterm Examination/Summer 2013/Dr. Daniel J. T.

Myles

1. Which of the following structures, including formal charges, is correct for

nitromethane, CH3NO2?

(A) H
O
H N
C O
H

(B) O
H N
C O
H
H

(C)
H O O
C N
H
H

(D) O
H N
C O
H
H

(E) O
H N
C O
H
H

2. The B–H bond in the tetrahydroborate ion, BH4–, is formed by the overlap
of what two orbitals?

(A) sp3–sp3
(B) sp3–sp2
(C) sp2–sp2
(D) sp2–s
(E) sp3–s

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CH 331/1st Midterm Examination/Summer 2013/Dr. Daniel J. T. Myles

3. A carbon-hydrogen bond in ethane is best described as being

__________.

(A) essentially nonpolar

(B) highly polar
(C) resonance stabilized
(D) a multiple bond
(E) ionic

4. In the following compound, indicate the formal charge on all atoms except
hydrogen, from left to right.

H C N C O

(A) carbon 0; nitrogen –1; carbon +1; oxygen 0

(B) carbon –1; nitrogen –1; carbon 0; oxygen –1
(C) carbon 0; nitrogen –1; carbon 0; oxygen –1
(D) carbon 0; nitrogen +1; carbon 0; oxygen –1
(E) None of the choices are correct.

5. Which of the following is closest to the H–C–H bond angle in the methyl
anion, CH3–?

(A) 60 °
(B) 90 °
(C) 109.5 °
(D) 120 °
(E) 180 °

6. Of the molecules below, the bond in __________ is the most polar.

(A) HCl
(B) SiCl4
(C) BCl3
(D) PCl3
(E) Cl2

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CH 331/1st Midterm Examination/Summer 2013/Dr. Daniel J. T. Myles

7. The name of the molecule below is:

(A) 7,7 diethyl-5-isopropyl-3,4-dimethyldecane

(B) 7,7-diethyl-5-isopropyl-2,3-dimethyldecane
(C) 7,7-diethyl-4-isopropyl-2,3-dimethyldecane
(D) 4,4-diethyl-6-isopropyl-8,9-dimethyldecane
(E) 5,5-diethyl-1-isobutyl-3-isopropyloctane

8. The name of the molecule below is:

Cl

(A) 1-chloro-5-sec-butylcycloheptane
(B) 1-chloro-5-isobutylcycloheptane
(C) 1-isobutyl-5-chlorocycloheptane
(D) 1-sec-butyl-4-chlorocycloheptane
(E) 1-sec-butyl-5-chlorocycloheptane

9. The name of the molecule below is:

(A) trans-1-isopropyl-4-fluorocyclohexane
(B) cis-1-isopropyl-3-fluorocyclohexane
(C) trans-1-isopropyl-3-fluorocyclohexane
(D) cis-1-fluoro-3-isopropylcyclohexane
(E) trans-1-fluoro-3-isopropylcyclohexane

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 CH 331/1st Midterm Examination/Summer 2013/Dr. Daniel J. T. Myles

10. If a noncyclic alkane hydrocarbon contains 7 carbon atoms, how many

hydrogen atoms must it also contain?

(A) 7
(B) 9
(C) 13
(D) 14
(E) 16

11. How many constitutional isomers are possible for C6H14?

(A) 5
(B) 6
(C) 7
(D) 8
(E) 9

12. In the boat conformation of cyclohexane, the “flagpole” hydrogen atoms

are located:

(A) on C-1 and C-3.

(B) on C-1 and C-4
(C) on the same carbon.
(D) on adjacent carbon atoms.
(E) none of the above

13. Which of the following is the staggered representation for rotation about
the C3–C4 bond in 2-methylhexane?

(A) (B) (C) (D) (E)

CH2CH3 CH(CH3)2 H H H CH2CH3

H H H H H H H H
CH2CH2CH(CH3)2
H3C CH3 H H H H H H H CH3
CH2CH3 CH2CH3 CH2CH2CH(CH3)2 H CH2CH3

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 CH 331/1st Midterm Examination/Summer 2013/Dr. Daniel J. T. Myles

14. Among the following conformers, which one occurs at highest energy on a
graph of potential energy versus dihedral angle for n-hexane?

(A) (B) (C) (D) (E)

H3CH2C CH3 H3CH2C CH2CH3 CH2CH3 CH3 CH3
H H H CH2CH3 H H

H H
H H H H H H H H H H
H H
CH2CH3 CH3 CH2CH3

15. trans-1,4-di-tert-butylcyclohexane contains how many axial substituents in

its most stable chair conformation?

(A) none
(B) 1
(C) 2
(D) 3
(E) impossible to know from the above information

16. Which of the following chiral compounds has an S configuration?

(A) (B) (C) (D) (E)

CH2CH3 CH2CH3 HO Br
CH3

H H
CH3 Br
Br CH2CH3

17. What term describes the structural relationship between cis-1,3-

dimethylcyclopentane and trans-1,2-dimethylcyclopentane?

(A) not isomers

(B) constitutional isomers
(C) enantiomers
(D) diastereomers

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CH 331/1st Midterm Examination/Summer 2013/Dr. Daniel J. T. Myles

18. The below structure is a synthetic precursor to cholesterol. How many

asymmetric carbon centers does it have?
OH

O
H H

(A) 6
(B) 7
(C) 8
(D) 9
(E) 15

19. An equal mixture of compounds A and B is:

F F

F F

A B

(A) optically active.

(B) optically inactive.
(C) you can’t tell.

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CH 331/1st Midterm Examination/Summer 2013/Dr. Daniel J. T. Myles

20. Which of the following is the enantiomer of the given compound?

Cl

Br

Cl Cl Cl Cl

Br
Cl Br

Br Br Br

(A) (B) (C) (D) (E)

21. What is the relationship between the structures shown below?

OH

OH

(A) enantiomers
(B) diastereomers
(C) constitutional isomers
(D) the same compound

22. Which of the following compounds has a stereoisomer that is a meso

compound? (I) 2,3-dibromobutane, (II) 1,2-dibromocyclopentane, (III) 1-
bromo-2-methylcyclobutane, (IV) 2,4-dimethylpentane, (V) 1,3-
dichlorocyclobutane?

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

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CH 331/1st Midterm Examination/Summer 2013/Dr. Daniel J. T. Myles

23. Predict the specific rotation of the compound shown.

Br Br

(A) It is impossible to predict; must be determined experimentally.

(B) Because both asymmetric centers are R, the compound is
dextrorotatory.
(C) Because both asymmetric centers are S, the compound is
levorotatory.
(D) Zero; the compound is achiral.
(E) Because this compound represents a racemic mixture, the
compound is dextrorotatory.

24. How many possible stereoisomers does 3,4,5,6-tetraethyldecane have?

(A) 2
(B) 4
(C) 8
(D) 15
(E) 16

25. What is the relationship between the structures shown below?

(A) they are constitutional isomers.

(B) they are identical.
(C) they are resonance structures.
(D) they are not isomers; they are different compounds.
(E) they are stereoisomers.

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