Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 9.2, Problem 16P

(a)

Interpretation Introduction

Interpretation:

Reason for reaction of alkyl halide with ammonia gives a low yield of primary amine but with azide ion gives a better yield has to be identified.

Concept Introduction:

  • The SN2  reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2  is a kind of nucleophilic substitution reaction mechanism.
  • The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.
  • The configuration of the product is inverted relative to the configuration of the reactant.

(b)

Interpretation Introduction

Interpretation:

The products obtained for the given SN2  reaction has to be drawn.

Concept Introduction:

  • The SN2  reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2  is a kind of nucleophilic substitution reaction mechanism.
  • The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.
  • The configuration of the product is inverted relative to the configuration of the reactant.

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1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.
3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in the reactant before being able to draw the arrows corresponding to product formation. A. B. Rearrangement ΘΗ
2. Draw the arrows required to make the following reactions occur. Please ensure your arrows point from exactly where you want to exactly where you want. If it is unclear from where arrows start or where they end, only partial credit will be given. Note: You may need to draw in lone pairs before drawing the arrows. A. B. H-Br 人 C Θ CI H Cl Θ + Br O

Chapter 9 Solutions

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