Question 1

Propose a synthesis of cyclopentanone from 1-methylcyclopentane.

Accepted Answer

The answer of Propose a synthesis of cyclopentanone from 1-methylcyclopentane....

Question 2

Which of the following alkenes cannot be converted into an alkyne by reacting it with bromine followed by an excess of sodium amide and then with water?

Accepted Answer

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

Question 3

Identify the statement that is not part of Green Chemistry.

Accepted Answer

A)  Energy efficiency. 
B)  Renewable feedstocks. 
C)  Reuse solvents without purification. 
D)  Prevent waste. 
E)  Use catalysts, rather that stoichiometric reagents. 
A)  Energy efficiency. 
B)  Renewable feedstocks. 
C)  Reuse solvents without purification. 
D)  Prevent waste. 
E)  Use catalysts, rather that stoichiometric reagents.

Question 4

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

Accepted Answer

1. Br₂, h

Question 5

Which sequence of reagents will accomplish the following synthesis?

Accepted Answer

A)  1. KOtBu; 2. HBr 
B)  1. NaOEt; 2. HBr, ROOR 
C)  1. H2SO4, heat; 2. Br2, h$\upsilon$ 
D)  1. NaOEt; 2. HBr 
E)  both A and D work 
A)  1. KOtBu; 2. HBr 
B)  1. NaOEt; 2. HBr, ROOR 
C)  1. H2SO4, heat; 2. Br2, h$\upsilon$ 
D)  1. NaOEt; 2. HBr 
E)  both A and D work

Question 6

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

Accepted Answer

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

Question 7

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

Accepted Answer

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

Question 8

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

Accepted Answer

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

Question 9

Propose a synthetic route for the following reaction.

Accepted Answer

1. Br₂, CCl

Question 10

Select the best reagents for the reaction below.

Accepted Answer

A)  NaNH2 
B)  1. O3; 2. H2O 
C)  KMnO4 
D)  1. BH3∙THF; 2. H2O2, NaOH 
E)  H2SO4, H2O 
A)  NaNH2 
B)  1. O3; 2. H2O 
C)  KMnO4 
D)  1. BH3∙THF; 2. H2O2, NaOH 
E)  H2SO4, H2O

Question 11

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 12

Select the best reagents for the reaction below.

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 
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

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

Accepted Answer

1. Conc. H

Question 14

Devise a synthetic route to convert ethylene into PVC (polyvinyl chloride).

Accepted Answer

The answer of Devise a synthetic route to convert ethylene...

Question 15

Perform a 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 
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 16

Select the best reagents for the reaction below.

Accepted Answer

A)  1. OsO4; 2. NaHSO3, H2O 
B)  1. Hg(OAc)2, H2O; 2. NaBH4 
C)  H2, Pt 
D)  1. 9-BBN; 2. H2O2, NaOH 
E)  1. O3; 2. DMS 
A)  1. OsO4; 2. NaHSO3, H2O 
B)  1. Hg(OAc)2, H2O; 2. NaBH4 
C)  H2, Pt 
D)  1. 9-BBN; 2. H2O2, NaOH 
E)  1. O3; 2. DMS

Question 17

Devise a synthetic route for the following equation.

Accepted Answer

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

Question 18

Select the best reagents for the reaction below.

Accepted Answer

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

Question 19

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

Accepted Answer

1. Br<sub>

Question 20

For multi-step reactions, which is the best method?

Accepted Answer

A)  two steps 
B)  three steps 
C)  four steps 
D)  five steps 
E)  six steps 
A)  two steps 
B)  three steps 
C)  four steps 
D)  five steps 
E)  six steps

Exam 11: Synthesis

Propose a synthesis of cyclopentanone from 1-methylcyclopentane.

Which of the following alkenes cannot be converted into an alkyne by reacting it with bromine followed by an excess of sodium amide and then with water?

Identify the statement that is not part of Green Chemistry.

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

Which sequence of reagents will accomplish the following synthesis?

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

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

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

Propose a synthetic route for the following reaction.

Select the best reagents for the reaction below.

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.

Select the best reagents for the reaction below.

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

Devise a synthetic route to convert ethylene into PVC (polyvinyl chloride).

Perform a 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).

Select the best reagents for the reaction below.

Devise a synthetic route for the following equation.

Select the best reagents for the reaction below.

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

For multi-step reactions, which is the best method?

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

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.