Question 1

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

Accepted Answer

1. Br₂, h

Question 2

Select the best reagents for the reaction below.

Accepted Answer

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

Question 3

Identify the best solvent for Green Chemistry.

Accepted Answer

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

Question 4

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

Accepted Answer

1. Br<sub>

Question 5

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. BH3∙THF; 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. BH3∙THF; 2. H2O2, NaOH 
E)  1. O3; 2. DMS

Question 6

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

Accepted Answer

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

Question 7

Propose a synthesis of propanoic acid from acetylene.

Accepted Answer

The answer of Propose a synthesis of propanoic acid from...

Question 8

Select the best reagents for the reaction below.

Accepted Answer

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

Question 9

Devise a synthetic route for the following equation.

Accepted Answer

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

Question 10

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

Accepted Answer

1. NaOEt
2

Question 11

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 
E)  hept-2-en-4-yne 
A)  hept-1-en-4-yne 
B)  hept-6-en-3-yne 
C)  hept-3-en-6-yne 
D)  hept-4-en-1-yne 
E)  hept-2-en-4-yne

Question 12

Provide the major product(s) for the following synthesis.

Accepted Answer

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

Question 13

Reaction of compound A (molecular formula = C7H12) with sodium amide, followed by reaction with 1-bromobutane produces a compound with a structure of (CH3)2CHCH(CH3)CC(CH2)3CH3. What is the name of compound A?

Accepted Answer

A)  2,3-dimethylnon-4-yne 
B)  2,2-dimethylpent-1-yne 
C)  3,4-dimethylpent-1-yne 
D)  4,4-dimethylhept-1-yne 
E)  1-heptyne 
A)  2,3-dimethylnon-4-yne 
B)  2,2-dimethylpent-1-yne 
C)  3,4-dimethylpent-1-yne 
D)  4,4-dimethylhept-1-yne 
E)  1-heptyne

Question 14

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 
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 15

Select the best reagents for the reaction below.

Accepted Answer

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

Question 16

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

Accepted Answer

1. tBuOK
2

Question 17

Propose a synthetic route for the following equation.

Accepted Answer

1. Br₂, h

Question 18

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

Accepted Answer

A)  1. Br2; 2. NaOH; 3. HBr 
B)  1. Br2, h$\upsilon$; 2. H2, Pt 
C)  1. H2, Pt; 2. Br2, h$\upsilon$ 
D)  1. NBS, h$\upsilon$; 2. H2, Pt 
E)  1. HBr, ROOR; 2. NaOH; 3. HBr 
A)  1. Br2; 2. NaOH; 3. HBr 
B)  1. Br2, h$\upsilon$; 2. H2, Pt 
C)  1. H2, Pt; 2. Br2, h$\upsilon$ 
D)  1. NBS, h$\upsilon$; 2. H2, Pt 
E)  1. HBr, ROOR; 2. NaOH; 3. HBr

Question 19

Most synthesis problems will have _________ (one, many) correct answers.

Accepted Answer

The answer of Most synthesis problems will have _________ (one,...

Question 20

Devise a synthetic route to prepare 1,3-dibromopropan-2-ol from propene.

Accepted Answer

The answer of Devise a synthetic route to prepare 1,3-dibromopropan-2-ol...

Exam 11: Synthesis

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

Select the best reagents for the reaction below.

Identify the best solvent for Green Chemistry.

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

Select the best reagents for the reaction below.

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

Propose a synthesis of propanoic acid from acetylene.

Select the best reagents for the reaction below.

Devise a synthetic route for the following equation.

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

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

Provide the major product(s) for the following synthesis.

Reaction of compound A (molecular formula = C7H12) with sodium amide, followed by reaction with 1-bromobutane produces a compound with a structure of (CH3)2CHCH(CH3)CC(CH2)3CH3. What is the name of compound A?

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?

Select the best reagents for the reaction below.

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

Propose a synthetic route for the following equation.

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

Most synthesis problems will have _________ (one, many) correct answers.

Devise a synthetic route to prepare 1,3-dibromopropan-2-ol from propene.

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

Reaction of compound A (molecular formula = C₇H₁₂) with sodium amide, followed by reaction with 1-bromobutane produces a compound with a structure of (CH₃)₂CHCH(CH₃)CC(CH₂)₃CH₃. What is the name of compound A?

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?