Question 1

Draw two possible sets of precursors that could be used to synthesize the target molecule below.

Accepted Answer

The answer of Draw two possible sets of precursors that...

Question 2

Show how the following could be synthesized from two separate alkynes,each with no more than four carbon atoms.

Accepted Answer

The answer of Show how the following could be synthesized...

Question 3

Write a synthetic step that shows the following reaction: 3-pentanone was treated first with lithium diisopropylamide.After this reaction was allowed to reach completion,the resulting product was treated with ethyl bromide to yield 4-methyl-3-hexanone as the overall product.

Accepted Answer

The answer of Write a synthetic step that shows the...

Question 4

Determine the overall percent yield for a five-step synthesis in which the yield of each individual step is 90%.

Accepted Answer

A) 90% 
B) 45% 
C) 59% 
D) 81% 
E) 33% 
A) 90% 
B) 45% 
C) 59% 
D) 81% 
E) 33%

Question 5

Determine the final product of the reaction sequence shown below.

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 6

Fill in the missing starting material needed to complete the following synthetic step.

Accepted Answer

The answer of Fill in the missing starting material needed...

Question 7

Supply the missing reagents necessary to complete the synthetic steps shown below,and indicate whether each step is a functional group conversion or a carbon-carbon bond formation reaction.

Accepted Answer

The answer of Supply the missing reagents necessary to complete...

Question 8

A researcher synthesizes 2-bromo-2-phenylpentane by reacting 2-phenyl-2-tosylpentane with potassium bromide.Write a synthetic step that shows this reaction,and draw the mechanism.

Accepted Answer

The answer of A researcher synthesizes 2-bromo-2-phenylpentane by reacting 2-phenyl-2-tosylpentane...

Question 9

Briefly explain why the synthetic step shown below is incorrect,and rewrite it so that it is correct.

Accepted Answer

The step shown is incorrect because chlo

Question 10

Which of the following solvents would not be a good choice to use when carrying out the reaction below?

Accepted Answer

A) DMSO 
B) CH3CH2CH2OH 
C) CH3OH 
D) DMF 
E) Ethyl acetate 
A) DMSO 
B) CH3CH2CH2OH 
C) CH3OH 
D) DMF 
E) Ethyl acetate

Question 11

Show how the following synthetic transformation could be carried out.

Accepted Answer

The answer of Show how the following synthetic transformation could...

Question 12

Choose the best precursors that could be used to synthesize the target molecule in the forward direction.

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 13

Which of the following is appropriate to include in a synthetic step but should not be included in the mechanism for a reaction?

Accepted Answer

A) Starting materials 
B) Mechanism arrows 
C) Products 
D) Reaction temperature 
E) Necessary reagents 
A) Starting materials 
B) Mechanism arrows 
C) Products 
D) Reaction temperature 
E) Necessary reagents

Question 14

Which of the following would yield the compound shown via an E2 reaction?

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 15

Which of the following steps would result in an alteration of the carbon skeleton?

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 16

Show how you would carry out the following transformation.

Accepted Answer

The answer of Show how you would carry out the...

Question 17

A student proposes the following synthetic step.Explain the potential error in this proposed step,and suggest a better alternative to carry out the desired synthetic transformation.

Accepted Answer

Subjecting an alkene to bromine in the p

Question 18

Which of the following solvents would be the best choice to use when carrying out the reaction below?

Accepted Answer

A) H2O 
B) CH3OH 
C) Acetic acid 
D) CH3CH2OH 
E) Cyclohexanol 
A) H2O 
B) CH3OH 
C) Acetic acid 
D) CH3CH2OH 
E) Cyclohexanol

Question 19

What is the missing starting material in the following synthetic sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 20

Which of the following synthetic steps is written correctly and would lead to the product shown?

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Exam 15: Organic Synthesis 1: Beginning Concepts

Draw two possible sets of precursors that could be used to synthesize the target molecule below.

Show how the following could be synthesized from two separate alkynes,each with no more than four carbon atoms.

Write a synthetic step that shows the following reaction: 3-pentanone was treated first with lithium diisopropylamide.After this reaction was allowed to reach completion,the resulting product was treated with ethyl bromide to yield 4-methyl-3-hexanone as the overall product.

Determine the overall percent yield for a five-step synthesis in which the yield of each individual step is 90%.

Determine the final product of the reaction sequence shown below.

Fill in the missing starting material needed to complete the following synthetic step.

Supply the missing reagents necessary to complete the synthetic steps shown below,and indicate whether each step is a functional group conversion or a carbon-carbon bond formation reaction.

A researcher synthesizes 2-bromo-2-phenylpentane by reacting 2-phenyl-2-tosylpentane with potassium bromide.Write a synthetic step that shows this reaction,and draw the mechanism.

Briefly explain why the synthetic step shown below is incorrect,and rewrite it so that it is correct.

Which of the following solvents would not be a good choice to use when carrying out the reaction below?

Show how the following synthetic transformation could be carried out.

Choose the best precursors that could be used to synthesize the target molecule in the forward direction.

Which of the following is appropriate to include in a synthetic step but should not be included in the mechanism for a reaction?

Which of the following would yield the compound shown via an E2 reaction?

Which of the following steps would result in an alteration of the carbon skeleton?

Show how you would carry out the following transformation.

A student proposes the following synthetic step.Explain the potential error in this proposed step,and suggest a better alternative to carry out the desired synthetic transformation.

Which of the following solvents would be the best choice to use when carrying out the reaction below?

What is the missing starting material in the following synthetic sequence?

Which of the following synthetic steps is written correctly and would lead to the product shown?

Atomic and Molecular Structure

Interchapter: Nomenclature 1-4

Interchapter 1molecular Orbital Theory and Chemical Reactions

Three-Dimensional Geometry,intermolecular Interactions,and Physical Properties

Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals

Isomerism 1: Conformational and Constitutional Isomers

Isomerism 2: Chirality,enantiomers,and Diastereomers

The Proton Transfer Reaction: an Introduction to Mechanisms,thermodynamics,and Charge Stability

An Overview of the Most Common Elementary Steps

An Introduction to Multistep Mechanisms: Sn1 and E1 Reactions

Nucleophilic Substitution and Elimination Reactions 1: Competition Among Sn2,sn1,e2,and E1 Reactions

Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful for Synthesis

Electrophilic Addition to Nonpolar Π Bonds 1: Addition of a Brønsted Acid

Electrophilic Addition to Nonpolar Π Bonds 2: Reactions Involving Cyclic Transition States

Orbital Interactions 2: Extended Π Systems,conjugation,and Aromaticity

Structure Determination 1: Ultravioletvisible and Infrared Spectroscopies

Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry

Nucleophilic Addition to Polar Π Bonds 1: Addition of Strong Nucleophiles

Nucleophilic Addition to Polar Π Bonds 2: Addition of Weak Nucleophiles and Acid and Base Catalysis

Organic Synthesis 2: Intermediate Topics in Synthesis Design,and Useful Reduction and Oxidation Reactions

Nucleophilic Additionelimination Reactions 1: the General Mechanism Involving Strong Nucleophiles

Nucleophilic Additionelimination Reactions 2: Weak Nucleophiles

Electrophilic Aromatic Substitution 1: Substitution on Benzene; Useful Accompanying Reactions

Electrophilic Aromatic Substitution 2: Substitution on Mono- and Disubstituted Benzene and Other Aromatic Rings

The Dielsalder Reaction and Other Pericyclic Reactions

Reactions Involving Free Radicals

Polymers

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