Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 7, Problem 51P

(a)

Interpretation Introduction

Interpretation:

The reason for obtaining a single pure product from hydroboration-oxidation of 2-butyne and two products from hydroboration-oxidation of 2-pentyne should be determined.

Concept Introduction:

Hydroboration-oxidation reaction:

  • Internal alkynes oxidize to form ketones.
  • Terminal alkyne oxidize to form aldehyde.
  • Reagents used are BH3andR2BH for internal alkyne.
  • R2BH is the reagent used for terminal alkynes.

General mechanism for hydroboration oxidation:

Organic Chemistry, Chapter 7, Problem 51P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The name of other two internal alkynes which yield only one product upon hydroboration-oxidation reaction has to be determined.

Concept Introduction:

Hydroboration-oxidation reaction:

  • Internal alkynes oxidize to form ketones.
  • Terminal alkyne oxidize to form aldehyde.
  • Reagents used are BH3andR2BH for internal alkyne.
  • R2BH is the reagent used for terminal alkynes.

General mechanism for hydroboration oxidation:

Organic Chemistry, Chapter 7, Problem 51P , additional homework tip  2

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Chapter 7 Solutions

Organic Chemistry

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 - Rank the following from strongest base to weakest...Ch. 7.12 - Prob. 26PCh. 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. 30PCh. 7 - What is each compounds systematic name?Ch. 7 - What reagents should be used to carry out the...Ch. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - What is the major product of the reaction of 1 mol...Ch. 7 - What is each compounds systematic name? a....Ch. 7 - What is the molecular formula of a hydrocarbon...Ch. 7 - Answer Problem 39, parts a-b, using 2-butyne as...Ch. 7 - Prob. 41PCh. 7 - a. Starting with 3-methyl 1-butyne, how can you...Ch. 7 - Prob. 43PCh. 7 - Which of the following pairs are keto-enol...Ch. 7 - Prob. 45PCh. 7 - Do the equilibria of the following acid-base...Ch. 7 - What stereoisomers are obtained when 2-butyne...Ch. 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. 51PCh. 7 - What stereoisomers are obtained from the following...Ch. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Prob. 55PCh. 7 - Prob. 56PCh. 7 - Prob. 57P
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