Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 21, Problem 5PP
PRACTICE PROBLEM 21.5
What is the product of the following Suzuki-Miyaura coupling?
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Compound A was prepared by sequential Suzuki cross-coupling reactions.First, compound 1 was treated with an aryl iodide to give compound 2, which was then treated with an aryl boronic acid to produce compound A.
How wood the structures for the aryl iodide, boronic acid, and compound 2 look like.
What aromatic product would you expect to obtain from oxidation of Tetralin with potassium permanganate solution. ( Write the chemical name of the product as your answer. Show the reaction scheme and mechanism)
Wolff-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.
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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- Compound 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_forwardBriefly explain why, under aqueous acidic conditions, furan readily undergoes a reversible ring opening reaction to give succinaldehyde.arrow_forwardWhen the nitrogen-containing aromatic heterocyclic compounds 1 and 2 are treated with HCl, only 1 forms the hydrochloride salt, whereas compound 2 is unreactive. Provide an explanation for this observed reactivity.arrow_forward
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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.arrow_forwardShow the structure of bromonium cation formed as an intermediate in bromination of trans-cinnamic acid. Clearly show stereochemistry at asymmetric carbons. Show, at which carbon nucleophilic attack of bromine anion is more likely. Explain why.arrow_forwardCompound A, C3H7Br, does not react with cold dilute potassium permanganate solution. Upon treatment with potassium hydroxide in ethanol, A gives only product B, C3H6. Unlike A, B decolourises potassium permanganate solution. Ozonolysis of Bgives C, C2H4O, and D, CH2O. Suggest the structural formulae of A, B, C and D.Write the equations for all the reactions involved.arrow_forward
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