Question 1

Propose a synthetic route for the following reaction.

Accepted Answer

1. NaCCH
2

Question 2

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$\upsilon$ 
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$\upsilon$

Question 3

Devise a synthetic route for the following equation.

Accepted Answer

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

Question 4

Identify the statement that is not part of Green Chemistry.

Accepted Answer

A)  Maximize atom economy. 
B)  Use safer solvents. 
C)  Prevent waste. 
D)  Run all reactions faster with high heat. 
E)  Use less hazardous reagents. 
A)  Maximize atom economy. 
B)  Use safer solvents. 
C)  Prevent waste. 
D)  Run all reactions faster with high heat. 
E)  Use less hazardous reagents.

Question 5

Which order of reactions would most effectively convert trans-2-butene into 1-butene?

Accepted Answer

A)  convert to the gem-dibromoalkane, then to the terminal alkyne, then to the terminal alkene 
B)  convert to an alcohol, then to a terminal alkyne, finally to the terminal alkene 
C)  convert to the terminal alkene in one step 
D)  shorten the chain by two carbons, then add a two-carbon alkene to the end 
E)  convert to an alkane, then to a terminal alkyne, and finally to a terminal alkene 
A)  convert to the gem-dibromoalkane, then to the terminal alkyne, then to the terminal alkene 
B)  convert to an alcohol, then to a terminal alkyne, finally to the terminal alkene 
C)  convert to the terminal alkene in one step 
D)  shorten the chain by two carbons, then add a two-carbon alkene to the end 
E)  convert to an alkane, then to a terminal alkyne, and finally to a terminal alkene

Question 6

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

Question 7

Select the best reagents for the reaction below.

Accepted Answer

A)  HBr 
B)  Br2/h$\upsilon$ 
C)  Br2, CCl4 
D)  HBr/ROOR 
E)  h$\upsilon$ /NBS 
A)  HBr 
B)  Br2/h$\upsilon$ 
C)  Br2, CCl4 
D)  HBr/ROOR 
E)  h$\upsilon$ /NBS

Question 8

One compound is produced when acetylene is treated with the following reagents. What is the product?

Accepted Answer

butanoic a

Question 9

Identify the changes that must occur in converting cis-2-butene into 2-butanol.

Accepted Answer

A)  only the identity of the functional group(s) must change 
B)  only the carbon skeleton must change 
C)  only the location of the functional group(s) must change 
D)  only the identity and location of the functional group(s) must change 
E)  both the carbon skeleton and the identity of the functional group(s) must change 
A)  only the identity of the functional group(s) must change 
B)  only the carbon skeleton must change 
C)  only the location of the functional group(s) must change 
D)  only the identity and location of the functional group(s) must change 
E)  both the carbon skeleton and the identity of the functional group(s) must change

Question 10

What is the minimum number of steps required to convert 2-methylpropane into 2-methylpropene?

Accepted Answer

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

Question 11

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

Accepted Answer

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

Question 12

Select the best reagents for the reaction below.

Accepted Answer

A)  HBr 
B)  Br2/h$\upsilon$ 
C)  Br2/ROOR 
D)  HBr/ROOR 
E)  h$\upsilon$ /NBS 
A)  HBr 
B)  Br2/h$\upsilon$ 
C)  Br2/ROOR 
D)  HBr/ROOR 
E)  h$\upsilon$ /NBS

Question 13

Predict a correct sequence of reactants required to complete the following synthesis in which propanal is the only carbon-containing product.   NaNH2 CH3SCH3 H2O CH3CH2Br O3 Na/NH3(l) H2/Pt I II III IV V VI VII

Accepted Answer

A)  1. I; 2. III; 3. IV; 4. V; 5. II 
B)  1. VI; 2. IV; 3. IV; 4. VII; 5. V; 6. II 
C)  1. V; 2. II 
D)  1. I; 2. IV; 3. VI; 4. V; 5. II 
E)  none of the above are correct 
A)  1. I; 2. III; 3. IV; 4. V; 5. II 
B)  1. VI; 2. IV; 3. IV; 4. VII; 5. V; 6. II 
C)  1. V; 2. II 
D)  1. I; 2. IV; 3. VI; 4. V; 5. II 
E)  none of the above are correct

Question 14

Devise a synthetic route to prepare 1,7-heptanediol from propene.

Accepted Answer

The answer of Devise a synthetic route to prepare 1,7-heptanediol...

Question 15

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

Question 16

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 17

Devise a synthesis to lengthen the legs of "Ralph" as requested below.

Accepted Answer

The answer of Devise a synthesis to lengthen the legs...

Question 18

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

Accepted Answer

1. Br₂, h

Question 19

Select the best reagent to convert 4,5-dimethylhex-2-yne to trans-4,5-dimethylhex-2-ene.

Accepted Answer

A)  1. OsO4; 2. NaHSO3, H2O 
B)  HBr, ROOR 
C)  NaBr 
D)  Na, NH3 
E)  HBr 
A)  1. OsO4; 2. NaHSO3, H2O 
B)  HBr, ROOR 
C)  NaBr 
D)  Na, NH3 
E)  HBr

Question 20

Predict the products of the following reaction.

Accepted Answer

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

Exam 11: Synthesis

Propose a synthetic route for the following reaction.

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

Devise a synthetic route for the following equation.

Identify the statement that is not part of Green Chemistry.

Which order of reactions would most effectively convert trans-2-butene into 1-butene?

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

Select the best reagents for the reaction below.

One compound is produced when acetylene is treated with the following reagents. What is the product?

Identify the changes that must occur in converting cis-2-butene into 2-butanol.

What is the minimum number of steps required to convert 2-methylpropane into 2-methylpropene?

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

Select the best reagents for the reaction below.

Predict a correct sequence of reactants required to complete the following synthesis in which propanal is the only carbon-containing product. NaNH2 CH3SCH3 H2O CH3CH2Br O3 Na/NH3(l) H2/Pt I II III IV V VI VII

Devise a synthetic route to prepare 1,7-heptanediol from propene.

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 alcohol (C).

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

Devise a synthesis to lengthen the legs of "Ralph" as requested below.

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

Select the best reagent to convert 4,5-dimethylhex-2-yne to trans-4,5-dimethylhex-2-ene.

Predict the products of the following reaction.

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

Predict a correct sequence of reactants required to complete the following synthesis in which propanal is the only carbon-containing product. NaNH₂ CH₃SCH₃ H₂O CH₃CH₂Br O₃ Na/NH₃(l) H₂/Pt I II III IV V VI VII