Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
Question
Book Icon
Chapter 6, Problem 39P

(a)

Interpretation Introduction

Interpretation: The mechanism using the curved-arrow notation should be written for the below reaction to get the major organic product.

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  1

Concept introduction: SN2 reactions are facile when the leaving group is good, nucleophile is sufficiently reactive and alkyl halide is a primary alkyl halide.

Leaving-group ability is determined by the capacity of leaving group to accommodate the negative charge as it is displaced from the alkyl halide. Among halogens, the iodides are best-leaving groups followed by bromide chloride and fluoride. Besides halides, some sulphonates and sulphate that can easily delocalize the negative charge can also behave as good leaving group. These include tosylate, mesylate and triflate.

In general, the weak conjugate bases that are derived from strong acids are also good leaving groups. The table for leaving groups on the basis of strength of bases is as follows:

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:The mechanism using the curved-arrow notation should be written for the below reaction to get the major organic product.

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  3

Concept introduction: SN2 reactions are facile when the leaving group is good, nucleophile is sufficiently reactive and alkyl halide is a primary alkyl halide.

Leaving-group ability is determined by the capacity of leaving group to accommodate the negative charge as it is displaced from the alkyl halide. Among halogens, the iodides are best-leaving groups followed by bromide chloride and fluoride. Besides halides, some sulphonates and sulphate that can easily delocalize the negative charge can also behave as good leaving group. These include tosylate, mesylate and triflate.

In general, the weak conjugate bases that are derived from strong acids are also good leaving groups. The table for leaving groups on the basis of strength of bases is as follows:

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  4

(c)

Interpretation Introduction

Interpretation:The mechanism using the curved-arrow notation should be written for the below reaction to get the major organic product.

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  5

Concept introduction: SN2 reactions are facile when the leaving group is good, nucleophile is sufficiently reactive and alkyl halide is a primary alkyl halide.

In general, the weak conjugate bases that are derived from strong acids are also good leaving groups. The table for leaving groups on the basis of strength of bases is as follows:

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  6

(d)

Interpretation Introduction

Interpretation:The mechanism using the curved-arrow notation should be written for the below reaction to get the major organic product.

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  7

Concept introduction:Leaving-group ability is determined by the capacity of leaving group to accommodate the negative charge as it is displaced from the alkyl halide. Among halogens, the iodides are best-leaving groups followed by bromide chloride and fluoride. Besides halides, some sulphonates and sulphate that can easily delocalize the negative charge can also behave as good leaving group. These include tosylate, mesylate and triflate.

(e)

Interpretation Introduction

Interpretation:The mechanism using the curved-arrow notation should be written for the below reaction to get the major organic product.

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  8

Concept introduction: SN2 reactions are facile when the leaving group is good, nucleophile is sufficiently reactive and alkyl halide is a primary alkyl halide.

Leaving-group ability is determined by the capacity of leaving group to accommodate the negative charge as it is displaced from the alkyl halide. Among halogens, the iodides are best-leaving groups followed by bromide chloride and fluoride. Besides halides, some sulphonates and sulphate that can easily delocalize the negative charge can also behave as good leaving group. These include tosylate, mesylate and triflate.

In general, the weak conjugate bases that are derived from strong acids are also good leaving groups. The table for leaving groups on the basis of strength of bases is as follows:

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  9

(f)

Interpretation Introduction

Interpretation:The mechanism using the curved-arrow notation should be written for the below reaction to get the major organic product.

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  10

Concept introduction: SN2 reactions are facile when the leaving group is good, nucleophile is sufficiently reactive and alkyl halide is a primary alkyl halide.

Leaving-group ability is determined by the capacity of leaving group to accommodate the negative charge as it is displaced from the alkyl halide. Among halogens, the iodides are best-leaving groups followed by bromide chloride and fluoride. Besides halides, some sulphonates and sulphate that can easily delocalize the negative charge can also behave as good leaving group. These include tosylate, mesylate and triflate.

In general, the weak conjugate bases that are derived from strong acids are also good leaving groups. The table for leaving groups on the basis of strength of bases is as follows:

  Organic Chemistry: Structure and Function, Chapter 6, Problem 39P , additional homework tip  11

Blurred answer
Students have asked these similar questions
4. Complete the phrases with one or more of the following terms: SNI, SN2, E1, E2. a) The reaction takes place in two or more steps. b) The reaction goes through a carbocation. c) The rate determining step has two reactants. d) The rate is independent of the concentration of nucleophile or base. e) Zaitsev's rule is often applicable to the products..
What type of mechanism is needed for this reaction?
What major product (from Figure #1) results from the following dehydration reaction (from Reaction #1)? Reaction #1 HO, H2SO4 heat Figure #1 compound A compound B compound C compound D Please click here if image does not display. In predicting the major product of boxed reaction #1, it is strongly recommended that you work out a complete mechanism on a piece of scratch paper. compound C compound A compound D compound B
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry: A Guided Inquiry
    Chemistry
    ISBN:9780618974122
    Author:Andrei Straumanis
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
    Text book image
    Pushing Electrons
    Chemistry
    ISBN:9781133951889
    Author:Weeks, Daniel P.
    Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Pushing Electrons
Chemistry
ISBN:9781133951889
Author:Weeks, Daniel P.
Publisher:Cengage Learning