Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
Question
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Chapter 6.10A, Problem 6.16P

(a)

Interpretation Introduction

To determine: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent).

Interpretation: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent) is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. There are two types of substitution reaction.

The nucleophilic reaction contains a substrate as well as a nucleophile as the reactants which mean a bimolecular nucleophilic reaction is termed as SN2 reaction. It includes the bond-making and bond-breaking steps. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

(b)

Interpretation Introduction

To determine: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent).

Interpretation: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent) is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. There are two types of substitution reaction.

The nucleophilic reaction contains a substrate as well as a nucleophile as the reactants which mean a bimolecular nucleophilic reaction is termed as SN2 reaction. It includes the bond-making and bond-breaking steps. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

(c)

Interpretation Introduction

To determine: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent).

Interpretation: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent) is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. There are two types of substitution reaction.

The nucleophilic reaction contains a substrate as well as a nucleophile as the reactants which mean a bimolecular nucleophilic reaction is termed as SN2 reaction. It includes the bond-making and bond-breaking steps. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

(d)

Interpretation Introduction

To determine: The stronger nucleophile among the given pairs of nucleophiles used in the SN2 reaction (using alcohol as a solvent).

Interpretation: The stronger nucleophile among the given pairs of nucleophiles used in the SN2 reaction (using alcohol as a solvent) is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. There are two types of substitution reaction.

The nucleophilic reaction contains a substrate as well as a nucleophile as the reactants which mean a bimolecular nucleophilic reaction is termed as SN2 reaction. It includes the bond-making and bond-breaking steps. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

(e)

Interpretation Introduction

To determine: The stronger nucleophile among the given pairs of nucleophiles used in the SN2 reaction (using alcohol as a solvent).

Interpretation: The stronger nucleophile among the given pairs of nucleophiles used in the SN2 reaction (using alcohol as a solvent) is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. There are two types of substitution reaction.

The nucleophilic reaction contains a substrate as well as a nucleophile as the reactants which mean a bimolecular nucleophilic reaction is termed as SN2 reaction. It includes the bond-making and bond-breaking steps. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

(f)

Interpretation Introduction

To determine: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent).

Interpretation: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent) is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. There are two types of substitution reaction.

The nucleophilic reaction contains a substrate as well as a nucleophile as the reactants which mean a bimolecular nucleophilic reaction is termed as SN2 reaction. It includes the bond-making and bond-breaking steps. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

(g)

Interpretation Introduction

To determine: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent).

Interpretation: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent) is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. There are two types of substitution reaction.

The nucleophilic reaction contains a substrate as well as a nucleophile as the reactants which mean a bimolecular nucleophilic reaction is termed as SN2 reaction. It includes the bond-making and bond-breaking steps. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

(h)

Interpretation Introduction

To determine: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent).

Interpretation: The stronger nucleophile among the given pairs of nucleophiles that is used in the SN2 reaction (using alcohol as a solvent) is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. There are two types of substitution reaction.

The nucleophilic reaction contains a substrate as well as a nucleophile as the reactants which mean a bimolecular nucleophilic reaction is termed as SN2 reaction. It includes the bond-making and bond-breaking steps. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

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Students have asked these similar questions
1. Which of the following is the strongest nucleophile? Refer to the diagram below with an MeOH, MeSH, etc. 2. Which of the following is true about the stereochemistry of SN1 reaction?a.retention of configuration at the electrophilic centerb.50:50 mixture of retention and inversion of configuration at the electrophilic centerc.inversion of configuration at the electrophilic centerd. slightly more inversion than retention at the electrophilic center
For each pair, predict the stronger nucleophile in the SN2 reaction (using an alcohol asthe solvent). Explain your prediction.(a) (CH3CH2)3N or (CH3CH2)2NH
Which nucleophile in each pair which would give the faster SN2 rate? (a) (CH3)2S or (CH3)2Se (b) (CH3)3CO- or CH3O-

Chapter 6 Solutions

Organic Chemistry (9th Edition)

Ch. 6.7 - Prob. 6.11PCh. 6.7 - Prob. 6.12PCh. 6.8 - Prob. 6.13PCh. 6.9 - Predict the major products of the following...Ch. 6.9 - Prob. 6.15PCh. 6.10A - Prob. 6.16PCh. 6.11A - When diethyl ether (CH3CH2OCH2CH3) is treated with...Ch. 6.11B - Prob. 6.18PCh. 6.11B - For each pair of compounds, state which compound...Ch. 6.12 - Prob. 6.20PCh. 6.12 - Under appropriate conditions...Ch. 6.13 - Propose an SN1 mechanism for the solvolysis of...Ch. 6.13B - Prob. 6.23PCh. 6.13B - 3-Bromocyclohexene is a secondary halide, and...Ch. 6.15 - Prob. 6.25PCh. 6.15 - Prob. 6.26PCh. 6.16 - For each reaction, give the expected substitution...Ch. 6.16 - Prob. 6.28PCh. 6.16 - Prob. 6.29PCh. 6 - Prob. 6.30SPCh. 6 - Draw the structures of the following compounds. a....Ch. 6 - Give systematic (IUPAC) names for the following...Ch. 6 - Prob. 6.33SPCh. 6 - Predict the compound in each pair that will...Ch. 6 - Prob. 6.35SPCh. 6 - Give two syntheses for (CH3)2CHOCH2CH3, and...Ch. 6 - Prob. 6.37SPCh. 6 - Prob. 6.38SPCh. 6 - Chlorocyclohexane reacts with sodium cyanide...Ch. 6 - Give the substitution products expected from...Ch. 6 - Prob. 6.41SPCh. 6 - Prob. 6.42SPCh. 6 - Two of the carbocations in Problem6-42 are prone...Ch. 6 - Prob. 6.44SPCh. 6 - Predict the products of the following SN2...Ch. 6 - Prob. 6.46SPCh. 6 - Strawberry growers have used large quantities of...Ch. 6 - A solution of pure (S)-2-iodobutane ([]=+15.90) in...Ch. 6 - Prob. 6.49SPCh. 6 - Give a mechanism to explain the two products...Ch. 6 - Prob. 6.51SPCh. 6 - Because the SN1 reaction goes through a flat...Ch. 6 - Prob. 6.53SPCh. 6 - Furfuryl chloride can undergo substitution by both...Ch. 6 - Prob. 6.55SPCh. 6 - The following reaction takes place under...Ch. 6 - Propose mechanisms to account for the observed...Ch. 6 - Prob. 6.58SPCh. 6 - Prob. 6.59SP
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