Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
Question
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Chapter 11, Problem 11.38P
Interpretation Introduction

(a)

Interpretation:

The reagent that is needed to convert to Organic Chemistry, Chapter 11, Problem 11.38P , additional homework tip  1 each of the compound needs to be identified.

Concept introduction:

Addition of H2O to an alkyne resembles similar to the acid-catalyzed addition of H2O to an alkene. In the presence of strong acid or Hg2+ catalyst, the elements of H2O add to the triple bond, an initial addition product of an enol is formed, which is an unstable product and rearranges to a product containing a carbonyl group-that is, a C=O. A carbonyl compound having two alkyl groups bonded to the C=O carbon is called a ketone product as shown below in the fig.

Organic Chemistry, Chapter 11, Problem 11.38P , additional homework tip  2

Interpretation Introduction

(b)

Interpretation:

The reagent that is needed to Organic Chemistry, Chapter 11, Problem 11.38P , additional homework tip  3 convert to each of the compound needs to be identified.

Concept introduction:

Addition of 1. R2BHand 2. H2O2, OH- reagent to an alkyne is a hydroboration-oxidation reaction to form the keto product as shown below in the fig. Addition of borane forms an organoborane. Oxidation with basic H20 2 forms an enol. Tautomerization of the enol forms a carbonyl compound. The overall result is addition of H2O to a triple bond.

Organic Chemistry, Chapter 11, Problem 11.38P , additional homework tip  4

Interpretation Introduction

(c)

Interpretation:

The reagent that is needed to convert to Organic Chemistry, Chapter 11, Problem 11.38P , additional homework tip  5 each of the compound needs to be identified.

Concept introduction:

Reaction between the 3-hexyne and HBr reagent is an example of electrophilic addition. The alkynes undergoes addition reaction because of pi bond in them. The electrophilic end of the reagent is attracted to the electron rich triple bond. It is a sequential reaction in which the addition of the reagent to alkyne to alkene which then addition of one more equivalent reagent to form the four new bond as alkane product as shown below in the fig.

Organic Chemistry, Chapter 11, Problem 11.38P , additional homework tip  6

Interpretation Introduction

(d)

Interpretation:

The reagent that is needed to Organic Chemistry, Chapter 11, Problem 11.38P , additional homework tip  7 convert to each of the compound needs to be identified.

Concept introduction:

Terminal alkynes are readily converted into acetylide anions using the strong bases such as NaNH2 and NaH. These anions are strong nucleophiles, capable of reacting with electrophiles such as alkyl halides and epoxides by nucleophilic substitution reaction is shown below in the fig.

Organic Chemistry, Chapter 11, Problem 11.38P , additional homework tip  8

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Chapter 11 Solutions

Organic Chemistry

Ch. 11 - Explain the following result. Although alkenes...Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.13PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.15PCh. 11 - Prob. 11.16PCh. 11 - Prob. 11.17PCh. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.19PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.21PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.23PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.25PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - Prob. 11.27PCh. 11 - Give the IUPAC name for each alkyne.Ch. 11 - Prob. 11.29PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.31PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.33PCh. 11 - Prob. 11.34PCh. 11 - Prob. 11.35PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - Draw the products formed when 3-hexyne is treated...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - What alkynes give each of the following ketones as...Ch. 11 - Prob. 11.41PCh. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - Prob. 11.43PCh. 11 - Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.45PCh. 11 - Prob. 11.46PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.52PCh. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - Prob. 11.55PCh. 11 - Synthesize each compound from acetylene. You may...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.61PCh. 11 - Prob. 11.62PCh. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.65PCh. 11 - Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.67PCh. 11 - 11.65 Explain why an optically active solution of ...
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