Introduction to General, Organic and Biochemistry
12th Edition
ISBN: 9780357391594
Author: Frederick A. Bettelheim; William H. Brown; Mary K. Campbell
Publisher: Cengage Learning US
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Chapter 12, Problem 44P
Propose an explanation for the following experimental observations:
- Acid-catalyzed hydration of 1-hexene gives a single alcohol in high yield.
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Acid-catalyzed dehydration of 3-methyl-2-butanol gives three alkenes: 2-methyl-2- butene, 3-methyl-1-butene, and 2-methyl-1-butene. Propose a mechanism to account for the formation of each product
Rank the following alcohols in order of increasing ease of acid-catalyzed dehydration. Provide the
structure of the dehydration product (alkene) from each alcohol.
OH
OH
3
1
a OH
Compound A, CH10, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction
over a Pd/C catalyst. On treatment of A with dilute H,SO, dehydration occurred and an optically inactive alkene B, CH4 was produced as the major
product. Alkene B, on ozonolysis, gave two products. Product C, C,H,0, was shown to be an aldehyde while product D, CHg0, was shown to be a ketone.
Draw the structure of compound C.
• You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms.
In cases where there is more than one answer, jtust draw one.
Chapter 12 Solutions
Introduction to General, Organic and Biochemistry
Ch. 12.3 - Prob. 12.1QCCh. 12.3 - Prob. 12.2QCCh. 12.3 - Problem 12-3 Write the IUPAC name for each...Ch. 12.3 - Problem 12-4 Draw structural formulas for the...Ch. 12.3 - Problem 12-5 How many stereoisomers are possible...Ch. 12.5 - Prob. 12.6QCCh. 12.5 - Problem 12-7 Propose a two-step mechanism for the...Ch. 12.5 - Prob. 12.8QCCh. 12.5 - Problem 12-9 Propose a three-step reaction...Ch. 12.5 - Prob. 12.10QC
Ch. 12.8 - Prob. 12.11QCCh. 12 - Prob. 1PCh. 12 - Answer true or false. Both ethylene and acetylene...Ch. 12 - 12-13 What is the difference in structure between...Ch. 12 - There are three compounds with the molecular...Ch. 12 - 12-15 Name and draw structural formulas for all...Ch. 12 - Prob. 6PCh. 12 - Draw a structural formula for at least one...Ch. 12 - Each carbon atom in ethane and in ethylene is...Ch. 12 - Prob. 9PCh. 12 - Prob. 10PCh. 12 - Prob. 11PCh. 12 - 12*22 Draw a structural formula for each compound....Ch. 12 - 12-23 Draw a structural formula for each compound....Ch. 12 - Prob. 14PCh. 12 - 12-25 Write the IUPAC name for each unsaturated...Ch. 12 - Explain why each name is incorrect and then write...Ch. 12 - 12-27 Explain why each name is incorrect and then...Ch. 12 - Prob. 18PCh. 12 - 12-29 Which of these alkenes show cis-trans...Ch. 12 - 12-30 Which of these alkenes shows cis-trans...Ch. 12 - 12-31 Cyclodecene exists as both cis and trans...Ch. 12 - Arachidonic acid is a naturally occurring C„o...Ch. 12 - Prob. 23PCh. 12 - If you examine the structural formulas for the...Ch. 12 - 12*35 For each molecule that shows eis-trans...Ch. 12 - Name and draw structural formulas for all...Ch. 12 - /3-Ocimene, a triene found in the fragrance of...Ch. 12 - Answer true or false. Alkenes and alkynes are...Ch. 12 - Prob. 29PCh. 12 - 12-40 Define alkene addition reaction. Write an...Ch. 12 - Prob. 31PCh. 12 - 12-42 Complete these equations.Ch. 12 - Draw structural formulas for all possible...Ch. 12 - Prob. 34PCh. 12 - 12-45 Draw a structural formula for the product of...Ch. 12 - Draw a structural formula for an alkene with the...Ch. 12 - 12-47 Draw a structural formula for an alkene with...Ch. 12 - Draw a structural formula for an alkene with the...Ch. 12 - Prob. 39PCh. 12 - 12-50 Draw the structural formula of an alkene...Ch. 12 - Prob. 41PCh. 12 - Prob. 42PCh. 12 - Following is the structural formula of...Ch. 12 - Propose an explanation for the following...Ch. 12 - There are nine alkenes with the molecular formula...Ch. 12 - Prob. 46PCh. 12 - 12-57 Hydrocarbon A, Cf,Hs, reacts with 2 moles of...Ch. 12 - 12-58 Show how to convert ethylene to these...Ch. 12 - 12-59 Show how to convert 1-butene to these...Ch. 12 - Prob. 50PCh. 12 - 12-61 (Chemical Connections 12A) What is one...Ch. 12 - Prob. 52PCh. 12 - Prob. 53PCh. 12 - 12-64 (Chemical Connections 120 What is the...Ch. 12 - (Chemical Connections 120 Assume that 1 X IO-12 g...Ch. 12 - Prob. 56PCh. 12 - Prob. 57PCh. 12 - Prob. 58PCh. 12 - Prob. 59PCh. 12 - Prob. 60PCh. 12 - Prob. 61PCh. 12 - Suppose you have unlabeled bottles of benzene and...Ch. 12 - Prob. 63PCh. 12 - Prob. 64PCh. 12 - Answer true or false. (a) Phenols and alcohols...Ch. 12 - Prob. 66PCh. 12 - Prob. 67PCh. 12 - Prob. 68PCh. 12 - Prob. 69PCh. 12 - 12-67 (Chemical Connections 12D ) In which isomer...Ch. 12 - Prob. 71PCh. 12 - Prob. 72PCh. 12 - Prob. 73PCh. 12 - Prob. 74PCh. 12 - Prob. 75PCh. 12 - Prob. 76PCh. 12 - Prob. 77PCh. 12 - Prob. 78PCh. 12 - Prob. 79PCh. 12 - Prob. 80PCh. 12 - Prob. 81PCh. 12 - Prob. 82PCh. 12 - Prob. 83PCh. 12 - Prob. 84PCh. 12 - Prob. 85PCh. 12 - Prob. 86PCh. 12 - Propose a structural formula for the product!s)...Ch. 12 - Prob. 88PCh. 12 - Draw the structural formula of an alkene that...Ch. 12 - 12-77 Show how to convert cyclopentene into these...Ch. 12 - Prob. 91PCh. 12 - Prob. 92PCh. 12 - Prob. 93PCh. 12 - Prob. 94PCh. 12 - Prob. 95PCh. 12 - In omega-3 fatty adds, the last carbon of the last...Ch. 12 - Prob. 97PCh. 12 - Prob. 98P
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