Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 12, Problem 12.12P
Interpretation Introduction

(a)

Interpretation: The product formed when the given compound is treated with H2 (excess), Pd-C is to be predicted.

Concept introduction: The addition of H2 in presence of catalyst is known as catalytic hydrogenation reaction. This is a syn addition. Alkyne is reduced to alkane. In this reaction, two weak pi bond of alkyne and sigma bond between H2 is broken and four CH bonds are formed.

Interpretation Introduction

(b)

Interpretation: The product formed when the given compound is treated with H2 (1 equiv.), Lindlar catalyst is to be predicted.

Concept introduction: The addition of H2 in presence of catalyst is known as catalytic hydrogenation reaction. Lindlar catalyst consists of palladium deposited on calcium carbonate which is poisoned or deactivated by lead or sulfur. In presence of Lindlar catalyst alkyne is reduced to cis-alkene.

Interpretation Introduction

(c)

Interpretation: The product formed when the given compound is treated with H2 (excess), Lindlar catalyst is to be predicted.

Concept introduction: The addition of H2 in presence of catalyst is known as catalytic hydrogenation reaction. Lindlar catalyst consists of palladium deposited on calcium carbonate which is poisoned or deactivated by lead or sulfur. In presence of Lindlar catalyst alkyne is reduced to cis-alkene.

Interpretation Introduction

(d)

Interpretation: The product formed when the given compound is treated with Na,NH3

is to be predicted.

Concept introduction: In presence of sodium metal in ammonia, the is alkyne is reduced to trans-alkene. The addition of H2 takes place in anti fashion to the triple bond. The mechanism involves the addition of electron followed by protonation.

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Chapter 12 Solutions

Organic Chemistry

Ch. 12 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Prob. 12.14PCh. 12 - Prob. 12.15PCh. 12 - Prob. 12.16PCh. 12 - Prob. 12.17PCh. 12 - Problem 12.18 Draw the products formed when both...Ch. 12 - Prob. 12.19PCh. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Prob. 12.22PCh. 12 - Prob. 12.23PCh. 12 - Problem 12.24 Draw the organic products in each of...Ch. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Problem 12.27 Draw the products of each Sharpless...Ch. 12 - Prob. 12.28PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 12.30PCh. 12 - 12.31 Devise a synthesis of the following compound...Ch. 12 - Label each reaction as oxidation, reduction, or...Ch. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - 12.37 Stearidonic acid (C18H28O2) is an...Ch. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Prob. 12.39PCh. 12 - Draw the organic products formed when allylic...Ch. 12 - Draw the organic products formed in each reaction...Ch. 12 - Draw the organic products formed in each reaction....Ch. 12 - Prob. 12.43PCh. 12 - Prob. 12.44PCh. 12 - Prob. 12.45PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - Prob. 12.47PCh. 12 - Draw the products formed after Steps 1 and 2 in...Ch. 12 - Prob. 12.49PCh. 12 - Prob. 12.50PCh. 12 - Prob. 12.51PCh. 12 - What alkyne gives each set of products after...Ch. 12 - Prob. 12.53PCh. 12 - Prob. 12.54PCh. 12 - Prob. 12.55PCh. 12 - 12.54 An unknown compound A of molecular formula ...Ch. 12 - 12.55 DHA is a fatty acid derived from fish oil...Ch. 12 - Prob. 12.58PCh. 12 - Prob. 12.59PCh. 12 - 12.58 Epoxidation of the following allylic alcohol...Ch. 12 - What allylic alcohol and DET isomer are needed to...Ch. 12 - Devise a synthesis of each hydrocarbon from...Ch. 12 - Prob. 12.63PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - Prob. 12.65PCh. 12 - Prob. 12.66PCh. 12 - Prob. 12.67PCh. 12 - Prob. 12.68PCh. 12 - Devise a synthesis of each compound from the...Ch. 12 - Devise a synthesis of each compound from acetylene...Ch. 12 - Prob. 12.71PCh. 12 - Prob. 12.72PCh. 12 - Prob. 12.73PCh. 12 - Prob. 12.74PCh. 12 - Prob. 12.75PCh. 12 - Prob. 12.76PCh. 12 - 12.72 Draw a stepwise mechanism for the following...Ch. 12 - Prob. 12.78PCh. 12 - Prob. 12.79PCh. 12 - Prob. 12.80PCh. 12 - 12.75 Sharpless epoxidation of allylic alcohol X...
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