Question 1

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

Accepted Answer

1) Br₂, h...

Question 2

Which of the following sequences of reagents will move the alcohol functional group from the tertiary position of 1-methyl-1-cyclohexanol to a secondary position?

Accepted Answer

A)   1)  KOtBu; 2)  Hg(OAc) 2, H2O; 3)  NaBH4
B)   1)  TsCl, pyr; 2)  KOtBu; 3)  BH3-THF; 4)  H2O2, NaOH
C)   1)  H2SO4, heat; 2)  BH3∙THF; 3)  H2O2, NaOH
D)   1)  TsCl, pyr; 2)  NaOH; 3)  BH3∙THF; 4)  H2O2, NaOH
E)   C and D will both work

Question 3

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

Accepted Answer

1) tBuOK 2...

Question 4

For the transformation shown, select the most appropriate reagent(s)  to effect the change. 4; 2)  NaHSO3, H2O B)  NaNH2 C)  H2, Pt D)  Na, NH3(l)  E)  H2, Lindlar's catalyst" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   1)  OsO4; 2)  NaHSO3, H2O
B)   NaNH2
C)   H2, Pt
D)   Na, NH3(l) 
E)   H2, Lindlar's catalyst

Question 5

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

Accepted Answer

1) Br₂, h...

Question 6

Which of the following sequences efficiently converts 2-methylpropene and sodium acetylide into 3-methylbutanal? 3; 4)  H2O B)  1)  HBr; 2)  NaCCH; 3)  O3; 4)  DMS C)  1)  HBr, ROOR; 2)  NaCCH; 3)  O3; 4)  H2O D)  1)  HBr, ROOR; 2)  NaCCH; 3)  H2/Ni2B 4)  O3; 5)  DMS E)  1)  NaCCH; 2)  H2/Ni2B; 3)  O3; 4)  DMS" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   1)  HBr; 2)  NaCCH; 3)  O3; 4)  H2O
B)   1)  HBr; 2)  NaCCH; 3)  O3; 4)  DMS
C)   1)  HBr, ROOR; 2)  NaCCH; 3)  O3; 4)  H2O
D)   1)  HBr, ROOR; 2)  NaCCH; 3)  H2/Ni2B 4)  O3; 5)  DMS
E)   1)  NaCCH; 2)  H2/Ni2B; 3)  O3; 4)  DMS

Question 7

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 compound shown (C) :

Accepted Answer

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

Question 8

For the transformation shown, select the most appropriate reagent(s)  to effect the change. 2/h 
u  C)  Br2 D)  HBr/ROOR E)  h 
u  /NBS " class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   HBr
B)   Br2/h ν
uν 
C)   Br2
D)   HBr/ROOR
E)   h ν
uν  /NBS

Question 9

Devise a method to complete the following synthesis.

Accepted Answer

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

Question 10

Propose an efficient synthesis of propanoic acid from acetylene:

Accepted Answer

The answer of Propose an efficient synthesis of propanoic acid...

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 alkene (C) :

Accepted Answer

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

Question 12

For the transformation shown, select the most appropriate reagent(s)  to effect the change. 2SO4 D)  NaOH E)  NaSH" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   NaOtBu
B)   HBr
C)   H2SO4
D)   NaOH
E)   NaSH

Question 13

Predict the major product(s)  for the reaction of pent-1-en-4-yne with sodium amide followed by reaction with bromoethane.

Accepted Answer

A)   Hept-1-en-4-yne
B)   Hept-6-en-3-yne
C)   Hept-3-en-6-yne
D)   Hept-4-en-1-yne

Question 14

What is the minimum number of steps required to convert 2-methylpropane into 1-bromo-2-methyl-2-propanol?

Accepted Answer

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

Question 15

Devise an efficient synthesis of the compound shown below starting with 4-methyl-2-pentanol.

Accepted Answer

The answer of Devise an efficient synthesis of the compound...

Question 16

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)  H2, Pt D)  1)  BH3∙THF; 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)   1)  Hg(OAc) 2, H2O; 2)  NaBH4
C)   H2, Pt
D)   1)  BH3∙THF; 2)  H2O2, NaOH
E)   1)  O3; 2)  DMS

Question 17

Provide the major product(s)  obtained from the following reaction:

Accepted Answer

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

Question 18

Devise a method to complete the following synthesis.

Accepted Answer

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

Question 19

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

Accepted Answer

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

Question 20

One compound is produced when acetylene is treated with the following reagents. What is the product?

Accepted Answer

The answer of One compound is produced when acetylene is...

Exam 12: Synthesis

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

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

Propose an efficient synthesis of propanoic acid from acetylene:

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

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Which of the following sequences efficiently converts 2-methylpropene and sodium acetylide into 3-methylbutanal?

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

Correct Answerverified1) tBuOK 2...View AnswerShow Answer

Devise a method to complete the following synthesis.

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Devise an efficient synthesis of the compound shown below starting with 4-methyl-2-pentanol.

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

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

Devise a method to complete the following synthesis.

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

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What is the minimum number of steps required to convert 2-methylpropane into 1-bromo-2-methyl-2-propanol?

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

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Provide the major product(s) obtained from the following reaction:

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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 alkene (C) :

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One compound is produced when acetylene is treated with the following reagents. What is the product?

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

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Predict the major product(s) for the reaction of pent-1-en-4-yne with sodium amide followed by reaction with bromoethane.

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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 compound shown (C) :

Correct AnswerverifiedShow Answer

Which of the following sequences of reagents will move the alcohol functional group from the tertiary position of 1-methyl-1-cyclohexanol to a secondary position?

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

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1) Br₂, h...
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For the transformation shown, select the most appropriate reagent(s) to effect the change. $For the transformation shown, select the most appropriate reagent(s) to effect the change. A) HBr B) Br<sub>2</sub>/h \nu C) Br<sub>2</sub> D) HBr/ROOR E) h \nu /NBS$

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1) tBuOK 2...
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1) Br₂, h...
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