Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Question
Chapter 5, Problem 5.5P
Interpretation Introduction
(a)
Interpretation:
The product formed by the acid-catalyzed hydration of
Concept introduction:
Hydration of
The general steps followed by the hydration reaction are stated below:
• First protonation of the alkene take place to generate the carbocation.
• Formation of protonated alcohol.
• Deprotonation.
Interpretation Introduction
(b)
Interpretation:
The product formed by the oxymercuration-reduction of
Concept introduction:
Oxymercuration-reduction is one of the methods used to convert alkenes into alcohols. This type of reaction follows Markovnikov’s rule.
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Acid-catalyzed hydration of 2-Methyl-1-butene yields two alcohols. The major product does not undergo oxidation, while the minor product will undergo oxidation. Explain why, by showing the structures of theproducts.
1) The carbon-oxygen double bond present in aldehydes and ketones is very polar. What does this mean and how does it arise?
2) The carbon-oxygen double bond is readily attacked by nucleophiles like cyanide ions or ammonia.
(i) What do you understand by the term nucleophile?
(ii) Which part of the carbon-oxygen double bond is attractive to nucleophiles?
3) Why is there a difference between aldehydes and ketones in their response to oxidizing agents such as potassium dichromate(VI) solution acidified with dilute sulfuric acid?
(1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case?
(2) Addition of HBr to 3,3-dimethyl-1-butene gives a mixture of two isomeric alkyl bromide products. Draw structures for the two products, and give a mechanistic explanation for their formation.
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 5.1PCh. 5 - Prob. 5.2PCh. 5 - Prob. 5.3PCh. 5 - Prob. 5.4PCh. 5 - Prob. 5.5PCh. 5 - Prob. 5.6PCh. 5 - Prob. 5.7PCh. 5 - Prob. 5.8PCh. 5 - Prob. 5.9PCh. 5 - Prob. 5.10P
Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Prob. 5.13PCh. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - Prob. 5.27APCh. 5 - Prob. 5.28APCh. 5 - Prob. 5.29APCh. 5 - Prob. 5.30APCh. 5 - Prob. 5.31APCh. 5 - Prob. 5.32APCh. 5 - Prob. 5.33APCh. 5 - Prob. 5.34APCh. 5 - Prob. 5.35APCh. 5 - Prob. 5.36APCh. 5 - Prob. 5.37APCh. 5 - Prob. 5.38APCh. 5 - Prob. 5.39APCh. 5 - Prob. 5.40APCh. 5 - Prob. 5.41APCh. 5 - Prob. 5.42APCh. 5 - Prob. 5.43APCh. 5 - Prob. 5.44APCh. 5 - Prob. 5.45APCh. 5 - Prob. 5.46APCh. 5 - Prob. 5.47APCh. 5 - Prob. 5.48APCh. 5 - Prob. 5.49APCh. 5 - Prob. 5.50APCh. 5 - Prob. 5.51APCh. 5 - Prob. 5.52APCh. 5 - Prob. 5.53APCh. 5 - Prob. 5.54AP
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