Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 12, Problem 12.39P
Interpretation Introduction

(a)

Interpretation:

To draw the organic products formed when 4-octyne is treated with given reagent.

Concept introduction:

Reduction of an alkyne by the addition of H2 to one or both of the pi bonds. When an alkyne is treated with two or more equivalents of H2 and using the Pd catalyst, reduction of both the pi bonds occurs. Syn addition of H2 to forms a cis alkene product and then form an alkane. Four new C-H bonds are formed.

Interpretation Introduction

(b)

Interpretation:

To draw the organic products formed when 4-octyne is treated with given reagent.

Concept introduction:

Reduction of an alkyne by the addition of H2 to one or both of the pi bonds. When an alkyne is treated with two or more equivalents of H2 and using the Pd catalyst, reduction of both the pi bonds occurs. Thus Palladium metal is too active a catalyst to allow the hydrogenation of an alkyne to stop after one equivalent of H2. Thus Lindlar catalyst is used to reduce the triple to double bond.

Interpretation Introduction

(c)

Interpretation:

To draw the organic products formed when 4-octyne is treated with given reagent.

Concept introduction:

Reduction of an alkyne by the addition of H2 to one or both of the pi bonds. When an alkyne is treated with two or more equivalents of H2 and using the Pd catalyst, reduction of both the pi bonds occurs. Using the Pd catalyst form the cis alkene or alkane product but not the trans alkene. Thus another reagent is used to reduce the triple to double in a trans form.

Interpretation Introduction

(d)

Interpretation:

To draw the organic products formed when 4-octyne is treated with given reagent.

Concept introduction:

Oxidative cleavage of an alkene breaks both the sigma and pi bonds of the double bond to form two carbonyl groups. Depending on the number of R groups bonded to the double bond, oxidative cleavage yields either ketones or aldehydes. But in the alkyne it is different. Alkynes undergoes Oxidative cleavage to form the two acids.

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Chapter 12 Solutions

Organic Chemistry-Package(Custom)

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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