Question 1

Which of the following effectively produces 4,4-dimethyl-2-pentyne?

Accepted Answer

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

Question 2

Propose a synthetic route to convert 3-methyl-2-butanol into 3-methyl-1-butanol.

Accepted Answer

The answer of Propose a synthetic route to convert 3-methyl-2-butanol...

Question 3

Select the best reagents for the reaction below.

Accepted Answer

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

Question 4

Select the best reagents for the reaction below.

Accepted Answer

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

Question 5

Taxol is found in the ______ tree

Accepted Answer

A) tea 
B) Eucalyptus 
C) sausage fruit 
D) Baobab 
E) Pacific yew 
A) tea 
B) Eucalyptus 
C) sausage fruit 
D) Baobab 
E) Pacific yew

Question 6

Devise a synthetic route for the following equation.

Accepted Answer

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

Question 7

Devise a synthetic route to convert methylcyclobutane into cyclopentene.

Accepted Answer

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

Question 8

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

Question 9

Devise a synthetic route to prepare 3-bromo-1-propanol from propene.

Accepted Answer

The answer of Devise a synthetic route to prepare 3-bromo-1-propanol...

Question 10

Propose a synthetic route to convert 3-methyl-1-butanol into 3-methyl-2-butanol.

Accepted Answer

The answer of Propose a synthetic route to convert 3-methyl-1-butanol...

Question 11

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 12

Taxol is a powerful _____.

Accepted Answer

A)  laxative 
B)  pain-killer 
C)  birth-control pill 
D)  anti-cancer drug 
E)  hallucinogen 
A)  laxative 
B)  pain-killer 
C)  birth-control pill 
D)  anti-cancer drug 
E)  hallucinogen

Question 13

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

Question 14

Devise a synthetic route of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

Accepted Answer

@#IMG-DLM&_TB4454_00 Alternati

Question 15

Propose a synthetic route for the following reaction.

Accepted Answer

1. NaOEt
2

Question 16

Select the best reagents for the reaction below.

Accepted Answer

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

Question 17

Perform a 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 
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 18

Which of the following provides a synthetic route to convert 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 
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

Question 19

Perform a 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 
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 20

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

Accepted Answer

1. Br₂, h

Exam 11: Synthesis

Which of the following effectively produces 4,4-dimethyl-2-pentyne?

Propose a synthetic route to convert 3-methyl-2-butanol into 3-methyl-1-butanol.

Select the best reagents for the reaction below.

Select the best reagents for the reaction below.

Taxol is found in the ______ tree

Devise a synthetic route for the following equation.

Devise a synthetic route to convert methylcyclobutane into cyclopentene.

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

Devise a synthetic route to prepare 3-bromo-1-propanol from propene.

Propose a synthetic route to convert 3-methyl-1-butanol into 3-methyl-2-butanol.

Select the best reagents for the reaction below.

Taxol is a powerful _____.

Select the best reagents for the reaction below.

Devise a synthetic route of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

Propose a synthetic route for the following reaction.

Select the best reagents for the reaction below.

Perform a 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).

Which of the following provides a synthetic route to convert 3-bromo-2-methyl-1-butene into 2-methyl-2-butene?

Perform a 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).

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

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

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