Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 9, Problem 9.25P

(a)

Interpretation Introduction

Interpretation:

The member that rapidly undergoes SN1 has to be selected from the given set (a).

Concept Introduction:

SN1Reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as SN1 unimolecular nucleophilic substitution.

The first step of SN1 is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  Rate= k[alkylhalide]

Nucleophile attacks the both front and back side of carbocation in SN1 reaction therefore result of this racemic product where formed.

Order of the substrate that favored in SN1 reaction is 3°>2°>1° .

(a)

Expert Solution
Check Mark

Answer to Problem 9.25P

The member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  1

Explanation of Solution

Given:

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  2

In SN1, rate determining step is formation of carbocation and order of the substrate that favored in SN1 reaction is 3°>2°>1°.

2-chloro-2 methyl propane gives more stable carbocation than 1-chlorobutane.

Hence, the member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  3

(b)

Interpretation Introduction

Interpretation:

The member that rapidly undergoes SN1 has to be selected from the given set (b).

Concept Introduction:

SN1reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as SN1 unimolecular nucleophilic substitution.

The first step of SN1 is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  Rate= k[alkylhalide]

Nucleophile attacks the both front and back side of carbocation in SN1 reaction therefore result of this racemic product where formed.

Order of the substrate that favored in SN1 reaction is 3°>2°>1° .

(b)

Expert Solution
Check Mark

Answer to Problem 9.25P

The member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  4

Explanation of Solution

Given:

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  5

Bromine is better leaving group than chlorine.

Hence, the member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  6

(c)

Interpretation Introduction

Interpretation:

The member that rapidly undergoes SN1 has to be selected from the given set (c).

Concept Introduction:

SN1reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as SN1 unimolecular nucleophilic substitution.

The first step of SN1 is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  Rate= k[alkylhalide]

Nucleophile attacks the both front and back side of carbocation in SN1 reaction therefore result of this racemic product where formed.

Order of the substrate that favored in SN1 reaction is 3°>2°>1° .

(c)

Expert Solution
Check Mark

Answer to Problem 9.25P

The member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  7

Explanation of Solution

Given:

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  8

In SN1, rate determining step is formation of carbocation and order of the substrate that favored in SN1 reaction is 3°>2°>1°.

Allyl cation is more stable than primary cation.

Hence, the member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  9

(d)

Interpretation Introduction

Interpretation:

The member that rapidly undergoes SN1 has to be selected from the given set (d).

Concept Introduction:

SN1reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as SN1 unimolecular nucleophilic substitution.

The first step of SN1 is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  Rate= k[alkylhalide]

Nucleophile attacks the both front and back side of carbocation in SN1 reaction therefore result of this racemic product where formed.

Order of the substrate that favored in SN1 reaction is 3°>2°>1°.

(d)

Expert Solution
Check Mark

Answer to Problem 9.25P

The member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  10

Explanation of Solution

Given:

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  11

In SN1, rate determining step is formation of carbocation and order of the substrate that favored in SN1 reaction is 3°>2°>1°.

Substuted allyllic cation is more stable than allylic cation.

Hence, the member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  12

(e)

Interpretation Introduction

Interpretation:

The member that rapidly undergoes SN1 has to be selected from the given set (e).

Concept Introduction:

SN1reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as SN1 unimolecular nucleophilic substitution.

The first step of SN1 is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  Rate= k[alkylhalide]

Nucleophile attacks the both front and back side of carbocation in SN1 reaction therefore result of this racemic product where formed.

Order of the substrate that favored in SN1 reaction is 3°>2°>1° .

(e)

Expert Solution
Check Mark

Answer to Problem 9.25P

The member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  13

Explanation of Solution

Given:

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  14

In SN1, rate determining step is formation of carbocation and order of the substrate that favored in SN1 reaction is 3°>2°>1°.

2-chloropentane gives more stable carbocation than 1-chloropentane.

Hence, the member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  15

(f)

Interpretation Introduction

Interpretation:

The member that rapidly undergoes SN1 has to be selected from the given set (f).

Concept Introduction:

SN1reaction: The displacement of atom or group by nucleophilic is known as nucleophilic substitution.

The rate of the reaction is depends on a single reactant in reaction is known as SN1 unimolecular nucleophilic substitution.

The first step of SN1 is formation of more stable carbocation then addition of nucleophile is the second step.

Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.

  Rate= k[alkylhalide]

Nucleophile attacks the both front and back side of carbocation in SN1 reaction therefore result of this racemic product where formed.

Order of the substrate that favored in SN1 reaction is 3°>2°>1°.

(f)

Expert Solution
Check Mark

Answer to Problem 9.25P

The member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  16

Explanation of Solution

Given:

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  17

In SN1, rate determining step is formation of carbocation and order of the substrate that favored in SN1 reaction is 3°>2°>1°.

Allylic cation is more stable than vinyl cation.

Hence, the member that rapidly undergoes SN1 is,

Organic Chemistry, Chapter 9, Problem 9.25P , additional homework tip  18

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Chapter 9 Solutions

Organic Chemistry

Ch. 9.9 - Prob. CQCh. 9.9 - Prob. DQCh. 9.10 - Prob. 9.9PCh. 9 - Prob. 9.10PCh. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Prob. 9.15PCh. 9 - Treatment of 1-aminoadamantane, C10H17N, with...Ch. 9 - Prob. 9.17PCh. 9 - Prob. 9.18PCh. 9 - Prob. 9.19PCh. 9 - Prob. 9.20PCh. 9 - Attempts to prepare optically active iodides by...Ch. 9 - Draw a structural formula for the product of each...Ch. 9 - Prob. 9.23PCh. 9 - Alkenyl halides such as vinyl bromide, CH2=CHBr,...Ch. 9 - Prob. 9.25PCh. 9 - Prob. 9.26PCh. 9 - Prob. 9.27PCh. 9 - Show how you might synthesize the following...Ch. 9 - Prob. 9.29PCh. 9 - 1-Chloro-2-butene undergoes hydrolysis in warm...Ch. 9 - Prob. 9.31PCh. 9 - Prob. 9.32PCh. 9 - Solvolysis of the following bicyclic compound in...Ch. 9 - Which compound in each set undergoes more rapid...Ch. 9 - Prob. 9.35PCh. 9 - Prob. 9.36PCh. 9 - Draw structural formulas for the alkene(s) formed...Ch. 9 - Prob. 9.38PCh. 9 - Following are diastereomers (A) and (B) of...Ch. 9 - Prob. 9.40PCh. 9 - Elimination of HBr from 2-bromonorbornane gives...Ch. 9 - Which isomer of 1-bromo-3-isopropylcyclohexane...Ch. 9 - Prob. 9.43PCh. 9 - Prob. 9.44PCh. 9 - Draw a structural formula for the major organic...Ch. 9 - When cis-4-chlorocyclohexanol is treated with...Ch. 9 - Prob. 9.47PCh. 9 - The Williamson ether synthesis involves treatment...Ch. 9 - The following ethers can, in principle, be...Ch. 9 - Prob. 9.50PCh. 9 - Prob. 9.51PCh. 9 - Prob. 9.52PCh. 9 - Prob. 9.53PCh. 9 - Prob. 9.54PCh. 9 - Write the products of the following sequences of...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Prob. 9.59PCh. 9 - Another important pattern in organic synthesis is...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - Prob. 9.64P
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