ORGANIC CHEMISTRY (LL)-PACKAGE
ORGANIC CHEMISTRY (LL)-PACKAGE
8th Edition
ISBN: 9781319316389
Author: VOLLHARDT
Publisher: MAC HIGHER
Question
Book Icon
Chapter 6, Problem 54P
Interpretation Introduction

Interpretation:The reason behind racemic mixture of iodoheptane products formed rather than pure (R)-2-iodoheptane should be explained.

Concept introduction:Bimolecular substitution or SN2 proceeds via single-step mechanism. Thus it is well known as concerted mechanism. Nucleophile approaches carbon while the leaving group still departs from the rear side (opposite to leaving group). The transition state only illustrates the geometric orientation of the substrates and reagents as they pass through the maxima in the single-step mechanism.

A general SN2 reaction mechanistic pathway is illustrated below:

  ORGANIC CHEMISTRY (LL)-PACKAGE, Chapter 6, Problem 54P

SN2 pathway as it is a stereospecific reaction. This essentially means the R stereoisomer can only lead to inverted S stereoisomer and vice versa. Thus the outcome is the rear side displacement of leaving group.

Polar-aprotic solvents accelerate the rate of SN2 reactions. These solvents possess partial positive and negative charges also. However, they do not liberate any proton to the substrate unlike water, methanol solvents. Acetone, DMSO, THF or DMF are categorized as polar aprotic solvent.

Blurred answer
Students have asked these similar questions
Please sirrr soollveee these parts pleaseeee and thank youuuuu
Please sirrr soollveee these parts pleaseeee and thank youuuuu, don't solve it by AI plleeaasseee
Please sirrr soollveee these parts pleaseeee and thank youuuuu
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • 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
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    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
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning