Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 21, Problem 10PP
Interpretation Introduction
Interpretation:
Reactants involved in the reactions to synthesize the products are to be determined.
Concept introduction:
Sonogashira coupling is the reaction in which an
It is a cross-coupling method and a very good method to join an
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Compound A has the molecular formula C14H25Br and was obtained by thereaction of sodium acetylide with 1,12-dibromododecane. On treatment ofcompound A with sodium amide, compound B (C14H24) was obtained. Ozonolysisof compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation ofcompound B over Lindlar palladium gave compound C (C14H26), andhydrogenation over platinum gave compound D (C14H28). Further, C yieldedO=CH(CH2)12CH=O on ozonolysis. Assign structures to compounds A through Dso as to be consistent with the observed transformations.
Chapter 21 Solutions
Organic Chemistry
Ch. 21 - PRACTICE PROBLEM 21.1
For each of the following...Ch. 21 - Prob. 2PPCh. 21 - PRACTICE PROBLEM 21.3 What product would you...Ch. 21 - Prob. 4PPCh. 21 - PRACTICE PROBLEM 21.5 What is the product of the...Ch. 21 - Prob. 6PPCh. 21 - Prob. 7PPCh. 21 - Prob. 8PPCh. 21 - Prob. 9PPCh. 21 - Prob. 10PP
Ch. 21 - Prob. 11PPCh. 21 - Practice Problem 21.12 What products would form...Ch. 21 - Prob. 13PCh. 21 - Prob. 14PCh. 21 - How would you synthesize each of the following...Ch. 21 - Prob. 16PCh. 21 - Predict the product(s) for each of the following...Ch. 21 - Prob. 18PCh. 21 - Prob. 19PCh. 21 - Prob. 20PCh. 21 - Prob. 21PCh. 21 - 21.22 Write a mechanism that can account for the...Ch. 21 - Prob. 23PCh. 21 - Prob. 24PCh. 21 - Prob. 25PCh. 21 - 21.26 In 1985, T. Katz (Columbia University)...Ch. 21 - When the following molecule was exposed to the...Ch. 21 - During the course of the following Stille...Ch. 21 - 1. In “The Chemistry of... Complex Cross...Ch. 21 - Prob. 2LGP
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- Deduce the structure of compound C.arrow_forwardCompound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.arrow_forwardWolff-Kishner reduction of compound W gave compound A. Treatment of A with m-chloroperbenzoic acid gave B which on reduction with LiAH4 gave C. Oxidation of compound C with chromic acid gave D (C9H14O). Suggest the structures for A, B, C, and D.arrow_forward
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