ORGANIC CHEMISTRY W/SSM >CB<
ORGANIC CHEMISTRY W/SSM >CB<
8th Edition
ISBN: 9781323748688
Author: Bruice
Publisher: PEARSON C
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Textbook Question
Chapter 7, Problem 29P

What is the major product obtained from the reaction of each of the following compounds with excess HCl?

  1. a. CH3CH2C≡CH
  2. b. CH3CH2C≡CCH2CH3
  3. c. CH3CH2C≡CCH2CH2CH3

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The major product obtained from the reaction of given compound with excess of HCl should be determined.

Concept Introduction:

Addition of halides to alkynes: Halogens like chlorine and bromine adds to the alkyne compounds.  The general form of the reaction is given below.

ORGANIC CHEMISTRY W/SSM >CB<, Chapter 7, Problem 29P , additional homework tip  1

If excess halides are present, a second addition reaction also occurs.

Answer to Problem 29P

The major product obtained from the reaction of given compound with excess of HCl is given below:

ORGANIC CHEMISTRY W/SSM >CB<, Chapter 7, Problem 29P , additional homework tip  2

Explanation of Solution

Hydrogen halides undergo addition reaction with alkynes.  Alkyne is a nucleophile and it reacts with the electrophile to give a π-complex.  In the next step, the halide ion adds to the π-complex and the product will be a halo-substituted alkene.  If excess reagent is present, another addition also occurs.

ORGANIC CHEMISTRY W/SSM >CB<, Chapter 7, Problem 29P , additional homework tip  3

In this reaction of butyne with HCl, a π complex is formed and then chloride ion adds to the π complex and chlorine substituted product is formed.  Here the reagent is excess HCl, therefore a second addition occurs and the final product is obtained.

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The major product obtained from the reaction of given compound with excess of HCl should be determined.

Concept Introduction:

Addition of halides to alkynes: Halogens like chlorine and bromine adds to the alkyne compounds.  The general form of the reaction is given below.

ORGANIC CHEMISTRY W/SSM >CB<, Chapter 7, Problem 29P , additional homework tip  4

If excess halides are present, a second addition reaction also occurs.

Answer to Problem 29P

The major product obtained from the reaction of given compound with excess of HCl is given below:

ORGANIC CHEMISTRY W/SSM >CB<, Chapter 7, Problem 29P , additional homework tip  5

Explanation of Solution

Hydrogen halides undergo addition reaction with alkynes.  Alkyne is a nucleophile and it reacts with the electrophile to give a πcomplex.  In the next step, the halide ion adds to the πcomplex and the product will be a halo-substituted alkene.  If excess reagent is present, another addition also occurs.

ORGANIC CHEMISTRY W/SSM >CB<, Chapter 7, Problem 29P , additional homework tip  6

In this reaction of hex-3-yne with HCl, a πcomplex is formed and then chloride ion adds to the πcomplex and chlorine substituted product is formed.  Here the reagent is excess HCl, therefore a second addition occurs and the final product is obtained.

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The major product obtained from the reaction of given compound with excess of HCl should be determined.

Concept Introduction:

Addition of halides to alkynes: Halogens like chlorine and bromine adds to the alkyne compounds.  The general form of the reaction is given below.

ORGANIC CHEMISTRY W/SSM >CB<, Chapter 7, Problem 29P , additional homework tip  7

If excess halides are present, a second addition reaction also occurs.

Answer to Problem 29P

The major product obtained from the reaction of given compound with excess of HCl is given below:

ORGANIC CHEMISTRY W/SSM >CB<, Chapter 7, Problem 29P , additional homework tip  8

Explanation of Solution

Hydrogen halides undergo addition reaction with alkynes.  Alkyne is a nucleophile and it reacts with the electrophile to give a πcomplex.  In the next step, the halide ion adds to the πcomplex and the product will be a halo-substituted alkene.  If excess reagent is present, another addition also occurs.

ORGANIC CHEMISTRY W/SSM >CB<, Chapter 7, Problem 29P , additional homework tip  9

In this reaction of hept-3-yne with HCl, a πcomplex is formed and then chloride ion adds to the πcomplex and chlorine substituted product is formed.  Here the reagent is excess HCl, therefore a second addition occurs and the final product is obtained.

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Chapter 7 Solutions

ORGANIC CHEMISTRY W/SSM >CB<

Ch. 7.6 - Prob. 12PCh. 7.6 - Prob. 13PCh. 7.7 - Prob. 14PCh. 7.7 - Which alkyne should be used for the synthesis of...Ch. 7.7 - Prob. 16PCh. 7.8 - Prob. 17PCh. 7.8 - Only one alkyne forms an aldehyde when it...Ch. 7.9 - Describe the alkyne you should start with and the...Ch. 7.9 - Prob. 20PCh. 7.10 - Prob. 21PCh. 7.10 - Prob. 22PCh. 7.10 - Prob. 23PCh. 7.10 - Rank the following from strongest base to weakest...Ch. 7.10 - Prob. 26PCh. 7.12 - Prob. 28PCh. 7 - What is the major product obtained from the...Ch. 7 - Draw a condensed structure for each of the...Ch. 7 - A student was given the structural formula of...Ch. 7 - Prob. 32PCh. 7 - What is each compounds systematic name?Ch. 7 - What reagents should be used to carry out the...Ch. 7 - Prob. 35PCh. 7 - Draw the mechanism for the following reaction:Ch. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - What is the major product of the reaction of 1 mol...Ch. 7 - Answer Problem 39, parts a-b, using 2-butyne as...Ch. 7 - What is each compounds systematic name? a....Ch. 7 - What is the molecular formula of a hydrocarbon...Ch. 7 - a. Starting with 3-methyl 1-butyne, how can you...Ch. 7 - Prob. 44PCh. 7 - Which of the following pairs are keto-enol...Ch. 7 - Prob. 46PCh. 7 - Do the equilibria of the following acid-base...Ch. 7 - What is each compounds systematic name?Ch. 7 - What stereoisomers are obtained when 2-butyne...Ch. 7 - Prob. 50PCh. 7 - Draw the keto tautomer for each of the following:Ch. 7 - Show how each of the following compounds can be...Ch. 7 - A chemist is planning to synthesize 3-octyne by...Ch. 7 - Prob. 54PCh. 7 - What stereoisomers are obtained from the following...Ch. 7 - Prob. 56PCh. 7 - Prob. 57PCh. 7 - Prob. 58PCh. 7 - Show how the following compound can be prepared...Ch. 7 - Prob. 60P
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