Question 1

Which statement below best explains why the Ka of acetylene is greater than that of ethylene?

Accepted Answer

A)   Acetylide anions are resonance stabilized.
B)   The 4  π\piπ  electrons of the acetylide anion better stabilize a negative charge.
C)   The electronegativity of sp carbons is greater than that of sp2 carbons.
D)   The electronegativity of sp carbons is less than that of sp2 carbons.
E)   Acetylene has only two hydrogen atoms while ethylene has four. F) A) and B)
G) A) and C)

Question 2

For the reaction below, which of the alkynes listed would be expected to produce the product under the conditions shown?

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) A) and D)
G) B) and D)

Question 3

For the reaction shown, select the expected major organic product.

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) B) and C)
G) B) and D)

Question 4

For the reaction shown, which of the compounds listed would be the expected enol intermediate?

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) All of the above
G) B) and E)

Question 5

For the reaction shown below, the resulting stereochemistry of the expected product is best described as:

Accepted Answer

A)   (R,
E)  
B)   (S,
E)  
C)   (R,Z) 
D)   (S,Z) 
E)   only (S) F) A) and B)
G) C) and D)

Question 6

A dihalide in which the halogens are attached on adjacent carbons is called a _______________ dihalide.

Accepted Answer

A)   vicinal
B)   geminal
C)   vinylic
D)   allylic
E)   cisF) B) and D)
G) B) and C)

Question 7

For the reaction shown, select the expected major organic product.

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) None of the above
G) A) and D)

Question 8

Identify the final product for the following reaction.

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) A) and E)
G) A) and D)

Question 9

Rank the following carbanions in order of increasing base strength.

Accepted Answer

A)   I 
B)   II 
C)   III 
D)   III 
E)   II < I < IIIF) All of the above
G) None of the above

Question 10

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)   (
E)  -4-isopropyloct-3-en-5-yne
B)   (Z) -4-isopropyloct-3-en-5-yne
C)   (
E)  -5-isopropyloct-5-en-3-yne
D)   (Z) -5-isopropyloct-5-en-3-yne
E)   (
E)  -4-(2-methylethyl) oct-3-en-5-yneF) D) and E)
G) C) and D)

Question 11

Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) C) and D)
G) A) and E)

Question 12

What is the expected major final product of the reaction sequence shown below?

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   None of the shown products will be produced.F) C) and D)
G) All of the above

Question 13

Determine which compound will react with sodium in liquid ammonia to form trans-3-hexene.

Accepted Answer

A)   cis-3-hexene
B)   trans-2-hexene
C)   3-hexyne
D)   2-hexyne
E)   cis-2-hexeneF) B) and D)
G) A) and E)

Question 14

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)   6-bromo-3-octyne
B)   6-bromo-6-methyl-3-heptyne
C)   2-bromo-2-methyl-4-heptyne
D)   6-bromo-6,6-dimethyl-3-hexyne
E)   2-bromo-4-octyneF) A) and E)
G) None of the above

Question 15

What is the expected major final product of the reaction sequence shown below?

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) B) and D)
G) A) and B)

Question 16

What is the IUPAC name for the molecule shown below?

Accepted Answer

A)   5,6,6-trimethyl-1-heptyne
B)   5-tert-butyl-1-hexyne
C)   2,2,3-trimethyl-6-heptyne
D)   2,2,3-(3-butynyl) butane
E)   sec-butyl-tert-butylacetyleneF) B) and E)
G) A) and D)

Question 17

For the reaction shown, select the expected major organic product.

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) B) and D)
G) C) and D)

Question 18

For the reaction shown, select the expected major organic product.

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   VF) B) and D)
G) None of the above

Question 19

Of the reaction conditions provided below, which would be expected to convert 1 mole of 4-methyl-1-pentyne into 2-methylpentane?

Accepted Answer

A)   H2, Lindlar's catalyst
B)   Na, NH3(l) 
C)   2 moles of HCl
D)   2 moles H2, Pt
E)   1 mole H2, PtF) B) and C)
G) A) and C)

Question 20

What is the major product of the reaction shown below?

Accepted Answer

A)   (
E)  -2,3-dichloro-2-hexene
B)   (Z) -2,3-dichloro-2-hexene
C)   2,2-dichlorohexane
D)   3,3-dichlorohexane
E)   2,2,3,3-tetrachlorohexaneF) A) and C)
G) All of the above

Exam 9: Alkynes

Which statement below best explains why the Ka of acetylene is greater than that of ethylene?

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What is the major product of the reaction shown below?

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A dihalide in which the halogens are attached on adjacent carbons is called a _______________ dihalide.

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What is the expected major final product of the reaction sequence shown below?

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What is the IUPAC name for the molecule shown below?

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For the reaction shown, select the expected major organic product.

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Identify the final product for the following reaction.

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For the reaction shown below, the resulting stereochemistry of the expected product is best described as:

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What is the IUPAC name for the molecule shown below?

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For the reaction below, which of the alkynes listed would be expected to produce the product under the conditions shown?

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What is the expected major final product of the reaction sequence shown below?

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For the reaction shown, select the expected major organic product.

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For the reaction shown, select the expected major organic product.

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For the reaction shown, which of the compounds listed would be the expected enol intermediate?

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What is the IUPAC name for the molecule shown below?

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Determine which compound will react with sodium in liquid ammonia to form trans-3-hexene.

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Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?

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For the reaction shown, select the expected major organic product.

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Rank the following carbanions in order of increasing base strength.

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Of the reaction conditions provided below, which would be expected to convert 1 mole of 4-methyl-1-pentyne into 2-methylpentane?

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Which statement below best explains why the K_a of acetylene is greater than that of ethylene?

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