Question 1

Devise a method of converting 4-methyl-1-pentene into 3-methylbutanoic acid.

Accepted Answer

The answer of Devise a method of converting 4-methyl-1-pentene into...

Question 2

Devise a synthetic route of the compound shown below starting with 4-methyl-2-pentanol.

Accepted Answer

The answer of Devise a synthetic route of the compound...

Question 3

Identify the solvent that is not recommended for Green Chemistry.

Accepted Answer

A)   methylene chloride
B)   water
C)   ethanol
D)   methanol
E)   ethyl acetate

Question 4

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

Question 5

Using retrosynthetic synthesis, 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)   IV

Question 6

Propose a synthesis of 1-butene from propyne.

Accepted Answer

The answer of Propose a synthesis of 1-butene from propyne....

Question 7

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

Accepted Answer

1. TsCl
2....

Question 8

Devise a synthetic route for the following equation.

Accepted Answer

The answer of Devise a synthetic route for the following...

Question 9

Select the best reagents for the reaction below. 2/h \upsilon  C)  Br2/ROOR D)  HBr/ROOR E)  h \upsilon  /NBS " class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   HBr
B)   Br2/h υ\upsilonυ 
C)   Br2/ROOR
D)   HBr/ROOR
E)   h υ\upsilonυ  /NBS

Question 10

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

Question 11

Select the best reagents for the reaction below. 4; 2. NaHSO3, H2O B)  H2SO4, H2O, HgSO4 C)  NaOH D)  excess NaNH2 E)  1. O3; 2. H2O" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   1. OsO4; 2. NaHSO3, H2O
B)   H2SO4, H2O, HgSO4
C)   NaOH
D)   excess NaNH2
E)   1. O3; 2. H2O

Question 12

Which of the following sequences 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 13

Propose a synthesis to produce the following answer as one of the major products.

Accepted Answer

1. NBS, h

2. H_2...

Question 14

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

Accepted Answer

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

Question 15

Select the best reagents for the reaction below. 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 16

Select the best reagents for the reaction below. 4; 2. NaHSO3, H2O B)  ROOR, heat C)  NaOH D)  excess 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)   excess NaNH2
E)   1. O3; 2. H2O

Question 17

The following sequence of reactions transforms acetylene into a compound with an altered carbon skeleton (compound 1) , and from that into a compound in which the functional group has been changed (compound 2) . Identify compounds 1 and 2.

Accepted Answer

A)   Compound 1 = I; Compound 2 = III
B)   Compound 1 = II; Compound 2 = III
C)   Compound 1 = VI; Compound 2 = IV
D)   Compound 1 = II; Compound 2 = IV
E)   Compound 1 = II; Compound 2 = V

Question 18

Select the best reagents for the reaction below. 2/H2O C)  Br2, CCl4 D)  HBr/ROOR E)  h \upsilon  /NBS " class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   HBr
B)   Br2/H2O
C)   Br2, CCl4
D)   HBr/ROOR
E)   h υ\upsilonυ  /NBS

Question 19

2-Methylpentane (C6H14) can be converted, through a multistep synthesis, to a compound with a molecular formula of C6H13Br that shows exactly six resonances in its proton-decoupled 13C NMR spectrum. Suggest a synthetic pathway to prepare such a compound from 2-methylpentane.

Accepted Answer

Question 20

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

Accepted Answer

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

Exam 11: Synthesis

The following sequence of reactions transforms acetylene into a compound with an altered carbon skeleton (compound 1) , and from that into a compound in which the functional group has been changed (compound 2) . Identify compounds 1 and 2.

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

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2-Methylpentane (C6H14) can be converted, through a multistep synthesis, to a compound with a molecular formula of C6H13Br that shows exactly six resonances in its proton-decoupled 13C NMR spectrum. Suggest a synthetic pathway to prepare such a compound from 2-methylpentane.

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Propose a synthesis to produce the following answer as one of the major products.

Correct Answerverified1. NBS, h2. H2...View AnswerShow Answer

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

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Devise a synthetic route for the following equation.

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

Correct Answerverified1. TsCl2....View AnswerShow Answer

Select the best reagents for the reaction below.

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Select the best reagents for the reaction below.

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Devise a synthetic route of the compound shown below starting with 4-methyl-2-pentanol.

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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?

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

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

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Identify the solvent that is not recommended for Green Chemistry.

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Devise a method of converting 4-methyl-1-pentene into 3-methylbutanoic acid.

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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 synthesis of 1-butene from propyne.

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Select the best reagents for the reaction below.

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Select the best reagents for the reaction below.

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Select the best reagents for the reaction below.

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2-Methylpentane (C₆H₁₄) can be converted, through a multistep synthesis, to a compound with a molecular formula of C₆H₁₃Br that shows exactly six resonances in its proton-decoupled ¹³C NMR spectrum. Suggest a synthetic pathway to prepare such a compound from 2-methylpentane.

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1. NBS, h
2. H_2...
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1. TsCl
2....
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Select the best reagents for the reaction below. $Select the best reagents for the reaction below. A) HBr B) Br<sub>2</sub>/H<sub>2</sub>O C) Br<sub>2</sub>, CCl<sub>4</sub> D) HBr/ROOR E) h \upsilon /NBS$

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Select the best reagents for the reaction below. $Select the best reagents for the reaction below. A) HBr B) Br<sub>2</sub>/h \upsilon C) Br<sub>2</sub>/ROOR D) HBr/ROOR E) h \upsilon /NBS$

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