Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Question
Chapter 18, Problem 23P
Interpretation Introduction
Interpretation:
The structural formula of the product formed in each of the given reactions is to be determined.
Concept Introduction:
▸ The
▸ Alkylation of the
▸ Decarboxylation of
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Students have asked these similar questions
(a)
(b)
(c)
Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw
the starting material(s), key reagent and a full reaction mechanism including an
explanation of the observed geometry.
Which of the following (B) and (C) will favour the enol form? Briefly explain your
reasoning.
Predict the product(s) and provide a mechanism for each of the following
transformations:
(i)
(ii)
OMe
OMe
Base
OEt
NaOEt
Draw a structural formula for the alcohol formed by treating each alkene with borane
in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide,
and specify stereochemistry where appropriate.
(a)
(d)
(b)
(e)
(c)
Explain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.
Chapter 18 Solutions
Organic Chemistry
Ch. 18 - Prob. 1PPCh. 18 - Practice Problem 18.2 Would optically active...Ch. 18 - Prob. 3PPCh. 18 - Practice Problem 18.4 Why do we say that the...Ch. 18 - Prob. 5PPCh. 18 - Practice Problem 18.6 (a) Write a reaction...Ch. 18 - PRACTICE PROBLEM 18.7
Show how you would use the...Ch. 18 - Practice Problem 18.8 The acetoacetic ester...Ch. 18 - Practice Problem 18.9
In the synthesis of the keto...Ch. 18 - PRACTICE PROBLEM 18.10 How would you use the...
Ch. 18 - PRACTICE PROBLEM 18.11
How would you use the...Ch. 18 - PRACTICE PROBLEM 18.12 Outline all steps in a...Ch. 18 - PRACTICE PROBLEM 18.13
The antiepileptic drug...Ch. 18 - PRACTICE PROBLEM 18.14 Show how you could employ...Ch. 18 - Prob. 15PCh. 18 - Treating a solution of cis-1-decalone with base...Ch. 18 - Prob. 17PCh. 18 - Prob. 18PCh. 18 - Prob. 19PCh. 18 - Prob. 20PCh. 18 - Prob. 21PCh. 18 - Prob. 22PCh. 18 - Prob. 23PCh. 18 - The synthesis of cyclobutanecarboxylic acid given...Ch. 18 - Prob. 25PCh. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Compound J, a compound with two four-membered...Ch. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - 18.32 Shown below is a synthesis of the elm bark...Ch. 18 - 18.33 (a) A compound U gives a negative iodoform...Ch. 18 - 18.34 Compound A has the molecular formula and...Ch. 18 - Prob. 35PCh. 18 - Prob. 36PCh. 18 - Prob. 37PCh. 18 - Prob. 38PCh. 18 - 1. -Carotene is a highly conjugated hydrocarbon...Ch. 18 - Dehydroabietic acid is a natural product isolated...
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- Provide reagentsarrow_forwardPredict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) anilinearrow_forwardDraw the structural formula(s) for the major product(s) of each of the following reactions. Unless required, ignore stereochemical details.arrow_forward
- 5.34 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol dovolonentanol or cyclohexanolarrow_forwardWhich of the following is the major product of the reaction below? (1) LDA/ether (2) (3) ethanol, A (A) (B) (C) (D) OCompound A Compound D Compound B Compound Carrow_forward4.33 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-Butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol (e) 1-Methylcyclopentanol or cyclohexanol Draw the energy diagrams of an SN1 reaction and an SN2 reaction. Include in your drawing anexample reaction. Identify the rate limiting step and label it as unimolecular or bimolecular.arrow_forward
- Predict the major organic product of each of the following reactions or provide the reagent needed to complete each transformation.arrow_forwardProvide the expected product for the reaction of each of the following alkenes with (i) HBr and (ii) HBr, H₂O₂. 3 (b) (c) (d) (e)arrow_forwardPredicts the major products for the following reaction.arrow_forward
- (b) A student wanted to synthesize methyl tert-butyl ether. He attempted the synthesis by adding sodium methoxide to tert-butyl chloride, but he obtained none of the desired product (1) (ii) Use an equation to show the product formed in this reaction Propose a suitable William ether synthetic route for methyl tert-butyl ether tach l.arrow_forward(a) Cyanohydrin formation is useful because of the further chemistry that can be carried out on the product. A nitrile can be reduced to yield a primary amine and also hydrolyzed to yield a carboxylic acid. Thus, cyanohydrin formation provides a method of transforming an aldehyde or ketone into a different functional group. Identify a series of synthetic transformation of the following reaction starting with benzaldehyde: (iii) (v) (i) H. (vi) (iv) (b) Treatment of an aldehyde or ketone with cyanide ion (:C=N), followed by protonation of the tetrahedral alkoxide ion intermediate, gives a cyanohydrin. Show the structure of the cyanohydrin obtained from cyclohexanone, with mechanistic explanation. HCNarrow_forward(b) State the reagents needed to convert benzoic acid into the following compounds. (i) C6H§COCI (ii) C,H$CH2OH (iii) C6H$CONHCH3arrow_forward
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