Question 1

Which of the following effectively produces 4,4-dimethyl-2-pentyne?

Accepted Answer

A)   
B)   
C)   
D)

Question 2

Show that you understand the concept of retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that could lead to the alkyl halide (C) :

Accepted Answer

A)   B = I and A = VIII
B)   B = VI and A = I
C)   B = III and A = VII
D)   B = IV and A = VII
E)   B = V and A = VIII

Question 3

Devise a method to complete the following synthesis.

Accepted Answer

The answer of Devise a method to complete the following...

Question 4

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

Accepted Answer

1) NaOEt 2...

Question 5

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

Accepted Answer

1) Br<sub>...

Question 6

Propose an efficient method of completing the following transformation:

Accepted Answer

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

Question 7

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

Accepted Answer

1) Br<sub>...

Question 8

Predict a correct sequence of reactants required to complete the following transformation in which propanal is the only carbon-containing product.

Accepted Answer

A)   1)  I; 2)  III; 3)  IV; 4)  V; 5)  II
B)   1)  VI; 2)  IV; 3)  IV; 4)  VII; 5)  V; 6)  II
C)   1)  V; 2)  II
D)   1)  I; 2)  IV; 3)  VI; 4)  V; 5)  II
E)   none of the above are correct

Question 9

Compound X has molecular formula C8H10. Reaction of Compound X with excess ozone, followed by reaction with dimethyl sulfide and then washing with water produces only the compounds shown below. Draw a possibility for Compound X that is consistent with these results.

Accepted Answer

Question 10

Devise a method of converting methylcyclobutane into cyclopentene.

Accepted Answer

The answer of Devise a method of converting methylcyclobutane into...

Question 11

Show that you understand the concept of retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that can lead to the alkyne (C) :

Accepted Answer

A)   B = I and A = VI
B)   B = VI and A = I
C)   B = III and A = VII
D)   B = IV and A = VII
E)   B = VI and A = VIII

Question 12

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)  DMS

Question 13

Devise a method to complete the following synthesis.

Accepted Answer

The answer of Devise a method to complete the following...

Question 14

For the transformation shown, select the most appropriate reagent(s)  to effect the change. 4; 2)  NaHSO3, H2O B)  H2SO4, H2O, HgSO4 C)  H2, Pt D)  1)  9-BBN; 2)  H2O2, NaOH 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)   H2, Pt
D)   1)  9-BBN; 2)  H2O2, NaOH
E)   1)  O3; 2)  DMS

Question 15

Which order of reactions would most effectively transform trans-2-butene into 1-butene?

Accepted Answer

A)   convert to the dibromoalkane, then to the terminal alkyne, then to the terminal alkene
B)   convert to an alcohol, then to a terminal alkyne, finally to the terminal alkene
C)   convert to the terminal alkene in one step
D)   shorten the chain by two carbons, then add a two-carbon alkene to the end
E)   convert to an alkane, then to a terminal alkyne, and finally to a terminal alkene

Question 16

What is the minimum number of steps required to convert 2-methylpropane into 2-methylpropene?

Accepted Answer

A)   1
B)   2
C)   3
D)   4
E)   5

Question 17

Propose an efficient method of completing the following transformation:

Accepted Answer

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

Question 18

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

Accepted Answer

1) Br₂, h...

Question 19

Propose an efficient method of completing the following transformation:

Accepted Answer

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

Question 20

Devise a synthesis to lengthen the legs of "Ralph" as requested below.

Accepted Answer

The answer of Devise a synthesis to lengthen the legs...

Exam 12: Synthesis

Propose an efficient method of completing the following transformation:

Correct AnswerverifiedShow Answer

Propose an efficient method of completing the following transformation:

Correct AnswerverifiedShow Answer

Show that you understand the concept of retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that can lead to the alkyne (C) :

Correct AnswerverifiedShow Answer

Propose an efficient method of completing the following transformation:

Correct AnswerverifiedShow Answer

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

Correct Answerverified1) Br2, h...View AnswerShow Answer

Compound X has molecular formula C8H10. Reaction of Compound X with excess ozone, followed by reaction with dimethyl sulfide and then washing with water produces only the compounds shown below. Draw a possibility for Compound X that is consistent with these results.

Correct AnswerverifiedShow Answer

Devise a method of converting methylcyclobutane into cyclopentene.

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What is the minimum number of steps required to convert 2-methylpropane into 2-methylpropene?

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

Correct AnswerverifiedShow Answer

Which of the following effectively produces 4,4-dimethyl-2-pentyne?

Correct AnswerverifiedShow Answer

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

Correct Answerverified1) NaOEt 2...View AnswerShow Answer

Devise a synthesis to lengthen the legs of "Ralph" as requested below.

Correct AnswerverifiedShow Answer

Show that you understand the concept of retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that could lead to the alkyl halide (C) :

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Devise a method to complete the following synthesis.

Correct AnswerverifiedShow Answer

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

Correct Answerverified1) Br...View AnswerShow Answer

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

Correct Answerverified1) Br...View AnswerShow Answer

Predict a correct sequence of reactants required to complete the following transformation in which propanal is the only carbon-containing product.

Correct AnswerverifiedShow Answer

Which order of reactions would most effectively transform trans-2-butene into 1-butene?

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Devise a method to complete the following synthesis.

Correct AnswerverifiedShow Answer

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1) Br₂, h...
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Compound X has molecular formula C₈H₁₀. Reaction of Compound X with excess ozone, followed by reaction with dimethyl sulfide and then washing with water produces only the compounds shown below. Draw a possibility for Compound X that is consistent with these results.

Correct Answer
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1) NaOEt 2...
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1) Br_...
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1) Br_...
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