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Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759
BuyFind

Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759

Solutions

Chapter
Section
Chapter 12, Problem 12.49P
Textbook Problem
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With the notable exception of ethanol, the acid- catalyzed hydration of alkenes cannot be used to prepare primary alcohols. It can only be used to prepare secondary and tertiary alcohols from alkenes in good yield. Explain why this is so and illustrate your reasoning with specific examples.

Expert Solution
Interpretation Introduction

Interpretation:

Why the acid-catalyzed hydration of alkenes cannot be used to prepare primary alcohol? And provide the reasoning as well.

Concept introduction:

During the hydration of alkene the unsaturated alkene converted into saturated alkane with the addition of H+ and OH- ions in the presence of H2 SO4. This reaction is carried out in the presence of acid therefore it is called acid catalyzed hydration of alkene.

Explanation of Solution

The hydration of alkene is an addition reaction of water in the presence of acid. Hence, this addition takes place as per the Markovnikov’s rule, which states that hydrogen atoms are added to carbons associated by a double bond carrying the greater number of hydrogen atoms. This forms carbonation and then a nucleophilic attack to form alcohol.

Only ethylene is a molecule which forms a primary carbocation, while in any other alkene, either 20 and 30 carbocations are formed, giving 20 and 30 alcohols. Only ethylene gives 10 alcohol.

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Chapter 12 Solutions

Introduction to General, Organic and Biochemistry
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Ch. 12 - Answer true or false. There are two classes of...Ch. 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 - Name and draw structural formulas for alkenes with...Ch. 12 - Draw a structural formula for at least one...Ch. 12 - Each carbon atom in ethane and in ethylene is...Ch. 12 - Prob. 12.19PCh. 12 - 12*20 Predict all bond angles about each...Ch. 12 - Answer true or false. The IUPAC name of an alkene...Ch. 12 - 12*22 Draw a structural formula for each compound....Ch. 12 - 12-23 Draw a structural formula for each compound....Ch. 12 - Prob. 12.24PCh. 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 - What structural feature in alkenes makes cis-trans...Ch. 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 - Following is the structural formula of a naturally...Ch. 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 - Answer true or false. Complete combustion of an...Ch. 12 - 12-40 Define alkene addition reaction. Write an...Ch. 12 - Prob. 12.41PCh. 12 - 12-42 Complete these equations.Ch. 12 - Draw structural formulas for all possible...Ch. 12 - 12-44 Draw a structural formula for the product...Ch. 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 - With the notable exception of ethanol, the acid-...Ch. 12 - 12-50 Draw the structural formula of an alkene...Ch. 12 - Acid-catalyzed hydration of 2-pentene gives a...Ch. 12 - Terpin, CloH20O2, is prepared commercially by the...Ch. 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. 12.56PCh. 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 - Answer true or false. Ethylene contains one...Ch. 12 - 12-61 (Chemical Connections 12A) What is one...Ch. 12 - (Chemical Connections 12B) Linolenic acid is a...Ch. 12 - (Chemical Connections 12C) What is the meaning of...Ch. 12 - 12-64 (Chemical Connections 120 What is the...Ch. 12 - (Chemical Connections 120 Assume that 1 X IO-12 g...Ch. 12 - (Chemical Connections 12D) What different func...Ch. 12 - 12-67 (Chemical Connections 12D ) In which isomer...Ch. 12 - (Chemical Connections 12E» What types of consumer...Ch. 12 - 12-69 (Chemical Connections 12E) In recycling...Ch. 12 - Write line-angle formulas for all compounds with...Ch. 12 - Refer to the structure of lycopene at the bottom...Ch. 12 - Prob. 12.72PCh. 12 - Prob. 12.73PCh. 12 - Propose a structural formula for the product!s)...Ch. 12 - cis-3-Hexene and fra ns-3-hexene are different...Ch. 12 - Draw the structural formula of an alkene that...Ch. 12 - 12-77 Show how to convert cyclopentene into these...Ch. 12 - In Chapter 21 on the biochemistry of lipids, we...Ch. 12 - The fatty acids in Problem 12-78 occur in animal...Ch. 12 - In omega-3 fatty adds, the last carbon of the last...Ch. 12 - Prob. 12.81P

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