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 13, Problem 68P
14-78 Consider
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МЕСНANISMS
1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed
opening of the epoxide ring to form two different products.
> Using ethanol as the solvent and an appropriate acid, show the steps in the acid
catalyzed mechanism, writing structures for all products of the steps. Circle the major
product(s).
> Using ethanol as the solvent and an appropriate base, show the steps in the base-
catalyzed mechanism, writing structures for all products of the steps. Circle the major
product(s).
1,2-epoxy-1-methylcyclopentane
CH3
Required answer for part (b) only
Chapter 13 Solutions
Introduction to General, Organic and Biochemistry
Ch. 13.1 - Prob. 13.1QCCh. 13.1 - Prob. 13.2QCCh. 13.2 - Problem 14-3 Draw structural formulas for the...Ch. 13.2 - Prob. 13.4QCCh. 13.2 - Prob. 13.5QCCh. 13.3 - Problem 14-6 Write the common name for each ether.Ch. 13.4 - Prob. 13.7QCCh. 13.4 - Prob. 13.8QCCh. 13 - 14-8 Answer true or false. The functional group of...Ch. 13 - 14-9 What is the difference in structure between a...
Ch. 13 - 14-10 Which of the following are secondary...Ch. 13 - 14-11 Which of the alcohols in Problem 14-10 are...Ch. 13 - 14-12 Write the 1UPAC name of each compound. (e)...Ch. 13 - Prob. 6PCh. 13 - Prob. 7PCh. 13 - 14-15 Both alcohols and phenols contain an —OH...Ch. 13 - Prob. 9PCh. 13 - 14-17 Explain in terms of noncovalent interactions...Ch. 13 - Prob. 11PCh. 13 - Prob. 12PCh. 13 - 14-20 Show hydrogen bonding between methanol and...Ch. 13 - 14-21 Show hydrogen bonding between the oxygen of...Ch. 13 - 14-22 Arrange these compounds in order of...Ch. 13 - 14-23 Arrange these compounds in order of...Ch. 13 - 14-24 2-Propanol (isopropyl alcohol) is commonly...Ch. 13 - Prob. 18PCh. 13 - Prob. 19PCh. 13 - Prob. 20PCh. 13 - 14-28 Give the structural formula of an alkene or...Ch. 13 - Prob. 22PCh. 13 - 14-30 Show how to distinguish between cyclohexanol...Ch. 13 - 14-31 Compare the acidity of alcohols and phenols,...Ch. 13 - 14-32 Both 2,6-diisopropylcyclohexanol and the...Ch. 13 - 14-33 Write equations for the reaction of...Ch. 13 - 14-34 Write equations for the reaction of...Ch. 13 - 14-35 Write equations for the reaction of each of...Ch. 13 - 14-36 Show how to convert cyclohexanol to these...Ch. 13 - Prob. 30PCh. 13 - Prob. 31PCh. 13 - 14-39 Name two important alcohols derived from...Ch. 13 - 14-40 Name two important alcohols derived from...Ch. 13 - Prob. 34PCh. 13 - 14-42 Write the common name for each ether. ch3...Ch. 13 - Prob. 36PCh. 13 - 14-44 Answer true or false. (a) The functional...Ch. 13 - Prob. 38PCh. 13 - Write the common name for each thiol in Problem 38...Ch. 13 - 14-47 Following are structural formulas for...Ch. 13 - 14-48 Explain why methanethiol, CH3SH, has a lower...Ch. 13 - 14-49 Answer true or false. Today, the major...Ch. 13 - (Chemical Connections 13A ) As stated in the...Ch. 13 - Prob. 44PCh. 13 - Prob. 45PCh. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - (Chemical Connections 13D ) Show that enflurane...Ch. 13 - Prob. 49PCh. 13 - 14-60 Write a balanced equation for the complete...Ch. 13 - 14-61 Knowing what you do about electronegativity,...Ch. 13 - 14-62 Draw structural formulas and write IUPAC...Ch. 13 - Prob. 53PCh. 13 - 14-64 Explain why the boiling point of ethylene...Ch. 13 - Prob. 55PCh. 13 - 14-66 1,4-Butanediol, hexane, and 1-pentanol have...Ch. 13 - 14-67 Of the three compounds given in Problem...Ch. 13 - Prob. 58PCh. 13 - 14-69 Show how to prepare each compound from...Ch. 13 - 14-70 Show how to prepare each compound from...Ch. 13 - 14-71 The mechanism of the acid-catalyzed...Ch. 13 - Prob. 62PCh. 13 - 14-73 Lipoic acid is a growth factor for many...Ch. 13 - 14-74 Following is a structural formula for the...Ch. 13 - Prob. 65PCh. 13 - Prob. 66PCh. 13 - Prob. 67PCh. 13 - 14-78 Consider alkenes A, B, and C. each of which...Ch. 13 - Prob. 69P
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