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 3PP
PRACTICE PROBLEM 21.3
What product would you expect from each of the following reactions?
(a)
(b)
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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.
Suggest reactivity of compound A, B and C in increasing order of E2 reaction
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.
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 produce compound D while undergo Friedel Crafts Alkylation. Compound D is then oxidized and produce compound E (C11H12O3) as a major product.What are the possible structural formula of compound D and E?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_forwardA certain compound is known to contain an aromatic benzene ring but failed to produce a fragrant yellow solution upon subjecting it to the nitration test. What may be a possible explanation for this? A. The benzene ring is part of a highly conjugated, blue dye molecule. B. The benzene ring contains a strong electron-withdrawing group. C. The benzene ring has no available sites left for electrophilic attack. D. All of the given. Kindly explain your answer in detail.arrow_forward
- Deduce the structure of compound C.arrow_forwardStarting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.) m-Chlorobenzoic acidarrow_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
- Suggest with explanation on how you would prepare the compound, 4-chloroaniline from anilinearrow_forwardSuggest reasonable explanations for each of the following: A. The rate of saponification of ethyl p-nitrobenzoate is 200 times faster than that of ethyl p-methoxybenzoate. B. The rate of saponification of methyl acetate, CH3CCO2CH3 is 50 times greater than that for isopropylacetate.arrow_forwardCompound 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.arrow_forward
- If you were ask to prepare ethylamine, suggest two ways which you would give that would give you exclusively the desired product. Explain what is happening in each reaction steps.arrow_forwardStarting with acid chloride with exactly 5 carbon atoms, and using appropriate reagents outline the synthesis of the following molecules:arrow_forwardCompound 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_forward
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