Question 1

Which one of the following alcohols would dehydrate most rapidly when treated with sulfuric acid?

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  V

Question 2

Which of these compounds would give the largest E2/SN2 product ratio on reaction with sodium ethoxide in ethanol at 55°C?

Accepted Answer

A)   N2 product ratio on reaction with sodium ethoxide in ethanol at 55°C? 
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Question 3

What are the major product(s) formed when trans-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol?

Accepted Answer

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

Question 4

Elimination reactions are favored over nucleophilic substitution reactions

Accepted Answer

A)  at high temperatures.
B)  when tert-butoxide ion is used.
C)  when 3 ∘\circ∘  alkyl halides are used as substrates.
D)  when nucleophiles are used which are strong bases and the substrate is a 2 ∘\circ∘ alkyl halide.
E)  in all of these cases.

Question 5

Which reaction would not result in alkylation of the acetylide anion as the major products?

Accepted Answer

A)   
B)   
C)   
D)   
E)  None of these choices.

Question 6

Which statement is/are true about acetylide anions?

Accepted Answer

A)  The alkylated product is poor with secondary alkyl halides.
B)  Primary alkyl halides are best suited for alkylation.
C)  In the presence of tertiary alkyl halides,the acetylide anion acts as base to give an elimination product.
D)  Only two of these statements are true.
E)  All of the statements are true.

Question 7

What would you expect to be the chief organic product(s) when 2-bromo-2-methylpentane react(s) with sodium propynide,i.e.,

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  V

Question 8

When 0.10 mol of ICH2CH2CH2CH2Cl reacts with 0.10 mol of NaOCH3 in CH3OH at 40 ∘\circ∘ C,the major product is:

Accepted Answer

A)  CH3OCH2CH2CH2CH2Cl
B)  CH3OCH2CH2CH2CH2I
C)  CH3OCH2CH2CH2CH2OCH3
D)  CH2=CHCH2CH2Cl
E)  CH2=CHCH2CH2I

Question 9

Rearrangements are likely to occur in which of the following reaction types?

Accepted Answer

A)  SN1 reactions
B)  SN2 reactions
C)  E1 reactions
D)  E2 reactions
E)  Both SN1 and E1 reactions

Question 10

If 0.10 mol of HSCH2CH2OH reacts at 25 ∘\circ∘ C,sequentially,with 0.20 mol of NaH,0.10 mol of CH3CH2Br followed by the addition of H2O,which is the major product?

Accepted Answer

A)  HSCH2CH2OCH2CH3
B)  CH3CH2SCH2CH2OH
C)  CH3CH2SCH2CH2OCH2CH3
D)  CH2=CH2
E)  CH3CH3

Question 11

Which alkyl halide,when treated with sodium ethoxide in ethanol,would afford a product mixture consisting of more than one elimination product?

Accepted Answer

A)  1-bromo-3,3-dimethylpentane
B)  1-bromo-2,3-dimethylpentane
C)  2-bromo-3,4-dimethylpentane
D)  2-bromo-3,3-dimethylpentane
E)  None of these choices would yield more than one elimination product.

Question 12

What would be the major product(s) of the following reaction?

Accepted Answer

A)  I
B)  II and III
C)  II,III,and IV
D)  III and IV
E)  None of these choices.

Question 13

The correct IUPAC name for the following compound is:

Accepted Answer

A)  (
E)  -2-Bromo-3-chloro-5-methyl-2-hexene
B)  (
E)  -2-Bromo-3-chloro-5-methyl-3-hexene
C)  (Z) -2-Bromo-3-chloro-5-methyl-3-hexene
D)  (Z) -2-Bromo-3-chloro-5-methyl-2-hexene
E)  (
E)  -2-Methyl-5-bromo-4-chloro-4-hexene

Question 14

What would be the major product(s) of the following reaction?

Accepted Answer

A)  I and III
B)  I and II
C)  II and III
D)  IV
E)  None of these choices.

Question 15

Predict the major product(s) for the following reaction sequence.

Accepted Answer

A)  A mixture of  and
B)   
C)   
D)   
E)  A mixture of two of these choices.

Question 16

By analyzing the starting material and the product(s) ,the following reaction is an example of what type of mechanism? N1 B) SN2 C) E1 D) E2 E) None of these choices." class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  SN1
B)  SN2
C)  E1
D)  E2
E)  None of these choices.

Question 17

Which of the following methods could be used to synthesize 4,4-dimethyl-2-hexyne?

Accepted Answer

A)   
B)   
C)   
D)  More than one of these choices.
E)  None of these choices.

Question 18

Which of the following compounds could be produced from the following reaction sequence?

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  mixture of III and IV

Question 19

What are the major product(s) formed when cis-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol?

Accepted Answer

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

Question 20

Which of the following reactions would yield 3,3-dimethyl-1-butene in a reasonable percentage yield (i.e.,greater than 50%) ?

Accepted Answer

A)   
B)   
C)  
D)  All of these choices.
E)  Only two of these choices.

Exam 7: Alkenes and Alkynes I

What would you expect to be the chief organic product(s) when 2-bromo-2-methylpentane react(s) with sodium propynide,i.e.,

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Predict the major product(s) for the following reaction sequence.

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Which of the following methods could be used to synthesize 4,4-dimethyl-2-hexyne?

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By analyzing the starting material and the product(s) ,the following reaction is an example of what type of mechanism?

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When 0.10 mol of ICH2CH2CH2CH2Cl reacts with 0.10 mol of NaOCH3 in CH3OH at 40 ∘\circ∘ C,the major product is:

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What would be the major product(s) of the following reaction?

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Elimination reactions are favored over nucleophilic substitution reactions

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What are the major product(s) formed when trans-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol?

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Which of the following reactions would yield 3,3-dimethyl-1-butene in a reasonable percentage yield (i.e.,greater than 50%) ?

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Which alkyl halide,when treated with sodium ethoxide in ethanol,would afford a product mixture consisting of more than one elimination product?

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Rearrangements are likely to occur in which of the following reaction types?

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What would be the major product(s) of the following reaction?

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Which reaction would not result in alkylation of the acetylide anion as the major products?

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Which statement is/are true about acetylide anions?

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Which of these compounds would give the largest E2/SN2 product ratio on reaction with sodium ethoxide in ethanol at 55°C?

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If 0.10 mol of HSCH2CH2OH reacts at 25 ∘\circ∘ C,sequentially,with 0.20 mol of NaH,0.10 mol of CH3CH2Br followed by the addition of H2O,which is the major product?

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Which of the following compounds could be produced from the following reaction sequence?

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Which one of the following alcohols would dehydrate most rapidly when treated with sulfuric acid?

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The correct IUPAC name for the following compound is:

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What are the major product(s) formed when cis-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol?

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When 0.10 mol of ICH₂CH₂CH₂CH₂Cl reacts with 0.10 mol of NaOCH₃ in CH₃OH at 40^$\circ$C,the major product is:

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Which of these compounds would give the largest E2/S_N2 product ratio on reaction with sodium ethoxide in ethanol at 55°C?

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If 0.10 mol of HSCH₂CH₂OH reacts at 25^$\circ$C,sequentially,with 0.20 mol of NaH,0.10 mol of CH₃CH₂Br followed by the addition of H₂O,which is the major product?

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