Organic Chemistry Chapter 7

1) How many elements of unsaturation are implied by the molecular formula C6H12?
A) 0
B) 1
C) 2
D) 3
E) 4
B) 1
2) How many elements of unsaturation are implied by the molecular formula c5h8O?
A) 0
B) 1
C) 2
D) 3
E) 4
C) 2
How many elements of unsaturation are implied by the molecular formula c7h11Cl?
A) 0
B) 1
C) 2
D) 3
E) 4
C) 2
4) How many elements of unsaturation are implied by the molecular formula C5H5NO2?
A) 0
B) 1
C) 2
D) 3
E) 4
E) 4
5) How many elements of unsaturation are implied by the molecular formula c8h11n?
A) 0
B) 1
C) 2
D) 3
E) 4
E) 4
18) Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below?

A) E
B) Z
C) neither E nor Z

C) neither E nor Z
19) Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below?

A) E
B) Z
C) neither E nor Z

B) Z
20) Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below?

A) E
B) Z
C) neither E nor Z

A) E
21) What two atomic orbitals or hybrid atomic orbitals overlap to form the C-H bond in ethylene?
A) C sp3 + H s
B) C sp2 + H s
C) C sp + H s
D) C p + H s
B) C sp2 + H s
22) What two atomic orbitals or hybrid atomic orbitals overlap to form the C-C ? bond in ethylene?
A) C sp3 + C sp3
B) C sp3 + C sp2
C) C sp2 + C sp2
D) C sp3 + C p
E) C sp2 + C p
C) C sp2 + C sp2
23) What two atomic orbitals or hybrid atomic orbitals overlap to form the C-C ? bond in ethylene?
A) C sp3 + C sp3
B) C sp3 + C sp2
C) C sp2 + C sp2
D) C sp2 + C p
E) C p + C p
E) C p + C p
24) Carbon-carbon single bonds tend to be __________ and __________ than carbon-carbon double bonds.
A) shorter, stronger
B) longer, stronger
C) shorter, weaker
D) longer, weaker
D) longer, weaker
31) Using Zaitsev’s rule, choose the most stable alkene among the following.
A) 1-methylcyclohexene
B) 3-methylcyclohexene
C) 4-methylcyclohexene
D) They are all of equal stability according to Zaitsev’s rule.
A) 1-methylcyclohexene
32) Using Zaitsev’s rule, choose the most stable alkene among the following.
A) hex-1-ene
B) (E)-hex-2-ene
C) (Z)-hex-2-ene
D) They are all of equal stability according to Zaitsev’s rule.
B) (E)-hex-2-ene
33) Using Zaitsev’s rule, choose the most stable alkene among the following.
A) 1,2-dimethylcyclohexene
B) 1,6-dimethylcyclohexene
C) cis-3,4-dimethylcyclohexene
D) They are all of equal stability according to Zaitsev’s rule.
A) 1,2-dimethylcyclohexene
40) Alkenes __________.
A) are relatively polar compounds
B) have lower boiling points than alcohols of similar molecular weight
C) are reasonably soluble in water
D) both A and B
E) none of the above
B) have lower boiling points than alcohols of similar molecular weight
53) Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give pent-2-ene as the only alkene product?
A) 1-chloropentane
B) 2-chloropentane
C) 3-chloropentane
D) 1-chloro-2-methylbutane
E) 1-chloro-3-methylbutane
C) 3-chloropentane
54) Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds via which of the following mechanistic pathways?
A) SN1
B) SN2
C) E1
D) E2
E) none of the above
D) E2
56) Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below?

A) E
B) Z
C) neither E nor Z

A) E
57) Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below?

A) E
B) Z
C) neither E nor Z

C) neither E nor Z
61) Which of the following statements best describes the relative bond dissociation energies of the sigma and pi bonds present in the carbon-carbon double bond of an alkene?
A) sigma > pi
B) pi > sigma
C) sigma = pi
D) cannot be estimated
A) sigma > pi
62) Which of the following best approximates the CCC bond angle of propene?
A) 90°
B) 109°
C) 120°
D) 150°
E) 180°
C) 120°
63) Consider molecules with the formula C10H16. Which of the following structural features are not possible within this set of molecules?
A) 2 triple bonds
B) 1 ring and 1 triple bond
C) 2 rings and 1 double bond
D) 2 double bonds and 1 ring
E) 3 double bonds
A) 2 triple bonds
65) Consider the constitutional isomers 2-methylbut-1-ene, 2-methylbut-2-ene, and 3-methylbut-1-ene. When each of these alkenes is subjected to catalytic hydrogenation (H2, Pt), a single product results. Which of the following best describes the structural relationship among these products?
A) The products are cis-trans isomers.
B) The products are identical.
C) The products are constitutional isomers.
D) The products are enantiomers.
E) The products are diastereomers.
B) The products are identical.
67) Which of the following alkenes is the major product when 2-bromo-2-methylpentane is treated with sodium ethoxide in ethanol?
A) 2-methylpent-1-ene
B) 2-methylpent-2-ene
C) (E)-4-methylpent-2-ene
D) (Z)-4-methylpent-2-ene
E) 4-methylpent-1-ene
B) 2-methylpent-2-ene
68) Which of the following alkenes is the major product when 2-bromo-2-methylpentane is treated with potassium tert-butoxide in tert-butanol?
A) 2-methylpent-1-ene
B) 2-methylpent-2-ene
C) (E)-4-methylpent-2-ene
D) (Z)-4-methylpent-2-ene
E) 4-methylpent-1-ene
A) 2-methylpent-1-ene
69) In the group shown below, which of the following alcohols is (are) likely to yield a product where skeletal rearrangement has occurred when treated with sulfuric acid?

3-methyl-3-pentanol, 3,3-dimethyl-2-butanol, 2,2-dimethylcyclohexanol

A) 3-methyl-3-pentanol only
B) 3,3-dimethyl-2-butanol only
C) 2,2-dimethylcyclohexanol only
D) both 3,3-dimethyl-2-butanol and 2,2-dimethylcyclohexanol
E) None of these three alcohols is prone to rearrangement.

D) both 3,3-dimethyl-2-butanol and 2,2-dimethylcyclohexanol
71) Dehydrohalogenation of an alkyl halide by treating it with a strong base to yield an alkene product typically occurs by what reaction mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) free radical
D) E2
72) Which of the following statements applies to the E2 mechanism?
A) It occurs with inversion of stereochemistry.
B) It occurs with racemization of stereochemistry.
C) It proceeds through the more stable carbocation intermediate.
D) The C-H and C-X bonds that break must be anti.
E) Use of a bulky base gives the more highly substituted alkene product.
D) The C-H and C-X bonds that break must be anti.
How many elements of unsaturation do molecules with a molecular formula of C6H6Cl6 have?
A) 0
B) 1
C) 2
D) 3
E) 4
B) 1
74) How many elements of unsaturation do molecules with a molecular formula of c8h4N2 have?
A) 2
B) 4
C) 6
D) 8
E) 10
D) 8
A newly isolated natural product was found to have the molecular formula C15H28O2. By hydrogenating a sample of the compound, it was determined to possess one p bond. How many rings are present in the compound?
A) 0
B) 1
C) 2
D) 3
E) 4
B) 1
85) Which of the following alkenes has the largest molar heat of hydrogenation (ie, releases the most heat upon hydrogenation)?
A) 2,3-dimethyl-2-butene
B) 2-methyl-2-butene
C) trans-2-butene
D) cis-2-butene
E) 1-hexene
E) 1-hexene
86) Which of the following alkenes has the smallest molar heat of hydrogenation (ie, releases the least heat upon hydrogenation)?
A) 2,3-dimethyl-2-butene
B) 2-methyl-2-butene
C) trans-2-butene
D) cis-2-butene
E) 1-hexene
A) 2,3-dimethyl-2-butene
92) Which of the following molecular formulas corresponds to a monocyclic saturated compound?
A) C6H6
B) C3H7Br
C) c3h7n
D) C3H8O
C) C3H7N
95) Which of the following cycloalkenes would be expected to be stable?

A) 1 & 2
B) 2 & 3
C) 2
D) 1 & 3
E) none are stable

D) 1 & 3
97) Identify the major product of the reaction below.

A)

B)

C)

D)

D)
98) Predict the major product of the reaction shown below.

A) 2,3-dimethyl-2-butene
B) 2,3-dimethyl-1-butene
C) 3,3-dimethyl-1-butene
D) None of the above

A) 2,3-dimethyl-2-butene
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