Question 1

Using retrosynthetic analysis, determine which compound(s)  could lead to the alkane shown below in a single step:

Accepted Answer

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

Question 2

Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

Accepted Answer

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Question 3

Propose a multi-step synthetic sequence to accomplish the transformation below.

Accepted Answer

The answer of Propose a multi-step synthetic sequence to accomplish...

Question 4

Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

Accepted Answer

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Question 5

For the transformation shown, select the most appropriate reagent(s)  to effect the change. 4; 2)  NaHSO3, H2O B)  H2SO4, H2O, HgSO4 C)  NaOH D)  xs NaNH2 E)  1)  O3; 2)  DMS" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   1)  OsO4; 2)  NaHSO3, H2O
B)   H2SO4, H2O, HgSO4
C)   NaOH
D)   xs NaNH2
E)   1)  O3; 2)  DMSF) A) and B)
G) A) and C)

Question 6

Devise a method of converting acetylene into the polymer shown below.

Accepted Answer

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Question 7

Reaction of compound A (molecular formula = C7H12)  with sodium amide followed by reaction with 1-bromobutane produces (CH3) 2CHCH(CH3) CC(CH2) 3CH3. What is the name of compound A?

Accepted Answer

A)   2,3-dimethylnon-4-yne
B)   2,2-dimethylpent-1-yne
C)   3,4-dimethylpent-1-yne
D)   4,4-dimethylhept-1-yne
E)   1-heptyneF) A) and C)
G) A) and D)

Question 8

Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

Accepted Answer

The answer of Propose an efficient synthesis of cyclopentanone from...

Question 9

Predict the major product(s)  for the following reaction:

Accepted Answer

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

Question 10

Select the best reagent to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1-yne.

Accepted Answer

A)   1)  OsO4; 2)  NaHSO3, H2O
B)   HBr, ROOR
C)   NaBr
D)   1)  xs NaNH2; 2)  H3O+
E)   HBrF) B) and C)
G) A) and D)

Question 11

Propose an efficient method of completing the following transformation:

Accepted Answer

The answer of Propose an efficient method of completing the...

Question 12

Propose an efficient synthesis of 1-butene from propyne:

Accepted Answer

The answer of Propose an efficient synthesis of 1-butene from...

Question 13

Starting with a primary alkyl bromide, which of the following results in an overall increase in the length of the carbon skeleton by one carbon?

Accepted Answer

A)   substitute bromide with acetylide, then cleave the triple bond.
B)   substitute bromide with acetylide, then reduce the alkyne to an alkene.
C)   substitute bromide with methoxide.
D)   eliminate hydrogen bromide to produce an alkene.E) A) and B)
F) All of the above

Question 14

Propose a strategy to prepare the target as one of the major products:

Accepted Answer

The answer of Propose a strategy to prepare the target...

Question 15

For the transformation shown, select the most appropriate reagent(s)  to effect the change. 4; 2)  NaHSO3, H2O B)  1)  Hg(OAc) 2, H2O; 2)  NaBH4 C)  1)  RCO3H; 2)  H3O+ D)  H2SO4, H2O E)  1)  O3; 2)  DMS" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   1)  OsO4; 2)  NaHSO3, H2O
B)   1)  Hg(OAc) 2, H2O; 2)  NaBH4
C)   1)  RCO3H; 2)  H3O+
D)   H2SO4, H2O
E)   1)  O3; 2)  DMSF) D) and E)
G) C) and E)

Exam 12: Synthesis

Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

Correct Answer
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Propose an efficient synthesis of 1-butene from propyne:

Correct Answer
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Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

Correct Answer
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Alternatively steps...
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For the transformation shown, select the most appropriate reagent(s) to effect the change.

Correct Answer
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Propose a strategy to prepare the target as one of the major products:

Correct Answer
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Predict the major product(s) for the following reaction:

Correct Answer
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Reaction of compound A (molecular formula = C₇H₁₂) with sodium amide followed by reaction with 1-bromobutane produces (CH₃) ₂CHCH(CH₃) CC(CH₂) ₃CH₃. What is the name of compound A?

Correct Answer
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For the transformation shown, select the most appropriate reagent(s) to effect the change.

Correct Answer
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Devise a method of converting acetylene into the polymer shown below.

Correct Answer
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Select the best reagent to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1-yne.

Correct Answer
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Propose an efficient method of completing the following transformation:

Correct Answer
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Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

Correct Answer
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Alternatively steps...
View Answer

Starting with a primary alkyl bromide, which of the following results in an overall increase in the length of the carbon skeleton by one carbon?

Correct Answer
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Propose a multi-step synthetic sequence to accomplish the transformation below.

Correct Answer
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Using retrosynthetic analysis, determine which compound(s) could lead to the alkane shown below in a single step:

Correct Answer
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Exam 12: Synthesis

Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

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Propose an efficient synthesis of 1-butene from propyne:

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Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

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For the transformation shown, select the most appropriate reagent(s) to effect the change.

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Propose a strategy to prepare the target as one of the major products:

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Predict the major product(s) for the following reaction:

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Reaction of compound A (molecular formula = C7H12) with sodium amide followed by reaction with 1-bromobutane produces (CH3) 2CHCH(CH3) CC(CH2) 3CH3. What is the name of compound A?

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For the transformation shown, select the most appropriate reagent(s) to effect the change.

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Devise a method of converting acetylene into the polymer shown below.

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Select the best reagent to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1-yne.

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Propose an efficient method of completing the following transformation:

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Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

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Starting with a primary alkyl bromide, which of the following results in an overall increase in the length of the carbon skeleton by one carbon?

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Propose a multi-step synthetic sequence to accomplish the transformation below.

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Using retrosynthetic analysis, determine which compound(s) could lead to the alkane shown below in a single step:

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Correct Answer
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Correct Answer
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Correct Answer
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Alternatively steps...
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Correct Answer
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Correct Answer
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Correct Answer
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Reaction of compound A (molecular formula = C₇H₁₂) with sodium amide followed by reaction with 1-bromobutane produces (CH₃) ₂CHCH(CH₃) CC(CH₂) ₃CH₃. What is the name of compound A?

Correct Answer
verified

Correct Answer
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Correct Answer
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Correct Answer
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Correct Answer
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Correct Answer
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Alternatively steps...
View Answer

Correct Answer
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Correct Answer
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Correct Answer
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