Question 1

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 2

Devise a method to complete the following synthesis.

Accepted Answer

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

Question 3

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

Accepted Answer

A)   1)  OsO4; 2)  NaHSO3, H2O
B)   HBr, ROOR
C)   NaBr
D)   xs NaNH2
E)   HBr

Question 4

Which sequence of reagents will accomplish the following transformation? 2SO4, heat; 2)  Br2, h 
u  D)  1)  NaOEt; 2)  HBr E)  both A and D work " class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   1)  KOtBu; 2)  HBr
B)   1)  NaOEt; 2)  HBr, ROOR
C)   1)  H2SO4, heat; 2)  Br2, h ν
uν 
D)   1)  NaOEt; 2)  HBr
E)   both A and D work

Question 5

Which of the following provides an efficient method of converting 3-bromo-2-methyl-1-butene into 2-methyl-2-butene?

Accepted Answer

A)   1)  NaOH; 2)  H2, Pt
B)   1)  H2, Pt; 2)  NaOEt
C)   1)  H2, Pt; 2)  Br2
D)   1)  H2, Ni2B; 2)  KOtBu
E)   1)  H2, Pt; 2)  KOtBu B

Question 6

Devise a method of converting trans-2-methyl-3-hexene into 5-methylhexanal.

Accepted Answer

The answer of Devise a method of converting trans-2-methyl-3-hexene into...

Question 7

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

Accepted Answer

1) TsCl 2)...

Question 8

Which of the following sequences most efficiently converts 3-methyl-1-pentene into 3-bromo-3-methylpentane?

Accepted Answer

A)   1)  Br2; 2)  NaOH; 3)  HBr
B)   1)  Br2, h ν
uν ; 2)  H2, Pt
C)   1)  H2, Pt; 2)  Br2, h ν
uν 
D)   1)  NBS, h ν
uν ; 2)  H2, Pt
E)   1)  HBr, ROOR; 2)  NaOH; 3)  HBr

Question 9

Provide the major product(s)  for the following transformation:

Accepted Answer

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

Question 10

Which sequence of reagents will accomplish the following transformation? 2; 2)  1-bromopropane C)  1)  NaNH2; 2)  2-bromopropane D)  1)  O3; 2)  DMS E)  1)  O3; 2)  1-bromopropane" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   1)  KOtBu; 2)  1-bromopropane
B)   1)  NaNH2; 2)  1-bromopropane
C)   1)  NaNH2; 2)  2-bromopropane
D)   1)  O3; 2)  DMS
E)   1)  O3; 2)  1-bromopropane

Question 11

For the transformation shown, select the most appropriate reagent(s)  to effect the change. 2SO4 C)  CH3CO2H D)  NaOEt E)  KOtBu" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   NaOH
B)   heat/H2SO4
C)   CH3CO2H
D)   NaOEt
E)   KOtBu

Question 12

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

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   I or II)  I, II, or IV

Question 13

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

Accepted Answer

A)   1)  OsO4; 2)  NaHSO3, H2O
B)   ROOR, heat
C)   NaOH
D)   xs NaNH2
E)   1)  O3; 2)  H2O

Question 14

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)  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)   1)  RCO3H; 2)  H3O+
D)   1)  BH3-THF; 2)  H2O2, NaOH
E)   1)  O3; 2)  DMS

Question 15

Select the best reagent to convert 1-bromo-1-methylcyclohexane to 1-bromo-2-methylcyclohexane.

Accepted Answer

A)   1)  KOtBu; 2)  HBr
B)   1)  NaOEt; 2)  HBr
C)   1)  NaOEt; 2)  HBr, ROOR
D)   1)  KOtBu; 2)  HBr, ROOR
E)   Br2, h ν
uν

Question 16

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 alcohol (C) :

Accepted Answer

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

Question 17

Reaction of compound A (molecular formula = C12H24)  with ozone followed by reaction with DMS produces only (CH3) 3CCH2CHO. Which of the following could be compound A?

Accepted Answer

A)   cis-2,3,7,8-tetramethyloct-4-ene
B)   trans-dodec-6-ene
C)   4,4-dimethylpent-1-ene
D)   cis-2,2,7,7-tetramethyloct-4-ene
E)   2,2-dimethyldec-4-ene

Question 18

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

Accepted Answer

1) Conc. H...

Question 19

Starting with a primary alkyl bromide, which of the following results in an overall decrease 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, then cleave the double bond. D

Question 20

Propose an efficient method of converting 3-methyl-2-butanol into 3-methyl-1-butanol.

Accepted Answer

The answer of Propose an efficient method of converting 3-methyl-2-butanol...

Exam 12: Synthesis

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

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

Correct AnswerverifiedShow Answer

Which sequence of reagents will accomplish the following transformation?

Correct AnswerverifiedShow Answer

Which of the following provides an efficient method of converting 3-bromo-2-methyl-1-butene into 2-methyl-2-butene?

Correct AnswerverifiedB

Devise a method of converting trans-2-methyl-3-hexene into 5-methylhexanal.

Correct AnswerverifiedShow Answer

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

Correct Answerverified1) TsCl 2)...View AnswerShow Answer

Which of the following sequences most efficiently converts 3-methyl-1-pentene into 3-bromo-3-methylpentane?

Correct AnswerverifiedShow Answer

Provide the major product(s) for the following transformation:

Correct AnswerverifiedShow Answer

Which sequence of reagents will accomplish the following transformation?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Select the best reagent to convert 1-bromo-1-methylcyclohexane to 1-bromo-2-methylcyclohexane.

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 alcohol (C) :

Correct AnswerverifiedShow Answer

Reaction of compound A (molecular formula = C12H24) with ozone followed by reaction with DMS produces only (CH3) 3CCH2CHO. Which of the following could be compound A?

Correct AnswerverifiedShow Answer

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

Correct Answerverified1) Conc. H...View AnswerShow Answer

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

Correct AnswerverifiedD

Propose an efficient method of converting 3-methyl-2-butanol into 3-methyl-1-butanol.

Correct Answerverified11eab459_a641_2e76_acdb_974ea06c9233_TB3185_00

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B

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1) TsCl 2)...
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Reaction of compound A (molecular formula = C₁₂H₂₄) with ozone followed by reaction with DMS produces only (CH₃) ₃CCH₂CHO. Which of the following could be compound A?

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1) Conc. H...
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D

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