The chemical behavior of 13C is essentially identical to that of 12C.If the reaction below is carried out,what percentage of the carbon atoms in the product will be 13C?

A) 0 percent B) 10 percent C) 20 percent D) 30 percent E) 50 percent A) 0 percent B) 10 percent C) 20 percent D) 30 percent E) 50 percent

Exam 19: Nucleophilic Addition to Polar Π Bonds 1: Addition of Strong Nucleophiles

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When the following compound is treated with dimethyl sulfide followed by sodium hydride,a product is formed whose formula is C₇H₁₂O.Draw a complete,detailed mechanism for this reaction,and predict the structure of the product.

(Short Answer)

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Question 21

Which of the following reagents would be the best choice to carry out the reaction shown below?

(Multiple Choice)

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Question 22

Predict the major product of the following synthetic scheme.

(Multiple Choice)

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Question 23

Which of the following is not a feasible Grignard reagent?

(Multiple Choice)

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Question 24

Which of the following functional groups contains a polar π bond with no leaving group?

(Multiple Choice)

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Question 25

Could the alkyl halide below be used to generate a sulfonium ylide? Show a mechanism to support your answer.

(Essay)

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Question 26

Which of the following compounds would you expect to react with a nucleophile at the highest rate?

(Multiple Choice)

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Question 27

Identify compounds X,Y,and Z in the three-step synthesis shown below.

(Short Answer)

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Question 28

Predict the major organic product and provide a detailed mechanism for the reaction that would occur in the molecule shown below.

(Short Answer)

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Question 29

Predict the major organic product for the following sequence of reactions.

(Short Answer)

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Question 30

The chemical behavior of ¹³C is essentially identical to that of ¹²C.If the reaction below is carried out,what percentage of the carbon atoms in the product will be ¹³C?

(Multiple Choice)

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Question 31

Which of the following molecules would be unlikely to undergo a nucleophilic addition reaction?

(Multiple Choice)

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Question 32

A reaction was carried out,and the two products shown below were obtained.Fill in the boxes with the starting material and the reagents that were used,and then draw a mechanism for the formation of the major product.

(Short Answer)

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Question 33

The Horner-Wadsworth-Emmons reaction is a modification of the Wittig reaction that utilizes a phosphonate-stabilized carbanion to produce an alkene.Propose a detailed mechanism for the Horner-Wadsworth-Emmons reaction shown below.

(Short Answer)

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Question 34

Two students decide to use different polar aprotic solvents to carry out the reaction below.Student A chooses acetonitrile,while student B chooses tetrahydrofuran.Which is the better choice,and why?

(Essay)

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Question 35

Which of the following nucleophiles would tend to favor conjugate addition to an α,β-unsaturated carbonyl?

(Multiple Choice)

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Question 36

Which of the following compounds would you expect to have the highest percent hydration at equilibrium?

(Multiple Choice)

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Question 37

Propose a detailed mechanism for the Knoevenagel condensation,shown below.

(Short Answer)

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Question 38

Which of the following compounds would you expect to react with a nucleophile at the lowest rate?

(Multiple Choice)

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Question 39

Choose an appropriate set of reagents to carry out the synthetic step shown below.

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Question 40

Showing 21 - 40 of 50

Exam 19: Nucleophilic Addition to Polar Π Bonds 1: Addition of Strong Nucleophiles

When the following compound is treated with dimethyl sulfide followed by sodium hydride,a product is formed whose formula is C7H12O.Draw a complete,detailed mechanism for this reaction,and predict the structure of the product.

Which of the following reagents would be the best choice to carry out the reaction shown below?

Predict the major product of the following synthetic scheme.

Which of the following is not a feasible Grignard reagent?

Which of the following functional groups contains a polar π bond with no leaving group?

Could the alkyl halide below be used to generate a sulfonium ylide? Show a mechanism to support your answer.

Which of the following compounds would you expect to react with a nucleophile at the highest rate?

Identify compounds X,Y,and Z in the three-step synthesis shown below.

Predict the major organic product and provide a detailed mechanism for the reaction that would occur in the molecule shown below.

Predict the major organic product for the following sequence of reactions.

The chemical behavior of 13C is essentially identical to that of 12C.If the reaction below is carried out,what percentage of the carbon atoms in the product will be 13C?

Which of the following molecules would be unlikely to undergo a nucleophilic addition reaction?

A reaction was carried out,and the two products shown below were obtained.Fill in the boxes with the starting material and the reagents that were used,and then draw a mechanism for the formation of the major product.

The Horner-Wadsworth-Emmons reaction is a modification of the Wittig reaction that utilizes a phosphonate-stabilized carbanion to produce an alkene.Propose a detailed mechanism for the Horner-Wadsworth-Emmons reaction shown below.

Two students decide to use different polar aprotic solvents to carry out the reaction below.Student A chooses acetonitrile,while student B chooses tetrahydrofuran.Which is the better choice,and why?

Which of the following nucleophiles would tend to favor conjugate addition to an α,β-unsaturated carbonyl?

Which of the following compounds would you expect to have the highest percent hydration at equilibrium?

Propose a detailed mechanism for the Knoevenagel condensation,shown below.

Which of the following compounds would you expect to react with a nucleophile at the lowest rate?

Choose an appropriate set of reagents to carry out the synthetic step shown below.

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

Organic Synthesis 1: Beginning Concepts

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 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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When the following compound is treated with dimethyl sulfide followed by sodium hydride,a product is formed whose formula is C₇H₁₂O.Draw a complete,detailed mechanism for this reaction,and predict the structure of the product.

The chemical behavior of ¹³C is essentially identical to that of ¹²C.If the reaction below is carried out,what percentage of the carbon atoms in the product will be ¹³C?