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Chapter 10: Problem 35

When isomeric alkenes are obtained in acid catalyzed dehydration of an alcohol, the alkene having the greater number of substituents on the double bond (the more stable alkene) generally predominates (Zaitsev's rule, Section 9.5).

Short Answer

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Question: Determine the major isomeric alkene obtained during the acid-catalyzed dehydration of the following alcohol: CH3-CH2-CH(OH)-CH3.

Step by step solution

01

Understand Acid-Catalyzed Dehydration of Alcohols

Acid-catalyzed dehydration of alcohols is an elimination reaction that involves the removal of an -OH group from the alcohol and one H atom from an adjacent carbon atom (beta-carbon) to form a C=C double bond (alkene). The reaction is facilitated by the presence of an acid catalyst, as it protonates the alcohol to form the more readily eliminated water molecule. The reaction involves a carbocation intermediate, which undergoes deprotonation to form the alkene.
02

Apply Zaitsev's Rule to Predict the Major Product

Zaitsev's rule states that the major product formed in an elimination reaction is the more stable alkene, which possesses a higher number of substituents on the double bond. The more substituted double bond stabilizes the alkene through hyperconjugation and inductive effects. Additionally, it is important to locate all possible beta-carbons, i.e., carbons adjacent to the alcohol-bearing carbon. Each beta-carbon can lead to a different alkene.
03

Identify the Alcohol and Possible Beta-Carbons

Examine the alcohol molecule for which the elimination reaction will occur. Identify the beta-carbons, the carbons directly adjacent to the one holding the -OH group.
04

Evaluate the Stability of the Alkenes Formed from Each Beta-Carbon Eliminations

For each beta-carbon, remove the -OH group from the alcohol and a hydrogen atom from the identified beta-carbon. Create a carbon-carbon double bond between the former alcohol-bearing carbon and the beta-carbon. Then, assess the substitution pattern of the formed alkene (mono-, di-, tri-, or tetrasubstituted).
05

Determine the Major Product

Based on Zaitsev's rule, the alkene formed from the elimination having the most substituents on the double bond will be the major (predominant) product in the reaction. By following these steps and applying Zaitsev's rule to acid-catalyzed dehydration of the given alcohol, one can determine the predominant isomeric alkene.

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Most popular questions from this chapter

Tertiary alcohols are resistant to oxidation because the carbon bearing the - OH is already bonded to three carbon atoms and, therefore, cannot form an additional caubon-axygen bond. 1-Methylcyclopentanod Thus, the prerequisite for the oxidation of an alcohol to an aldehyde or ketone is at least one Hon the carbon bearing the OH gromp.

From each pair of compounds, select the one that is more soluhle in water. (a) \(\mathrm{CH}_{2} \mathrm{Cl}_{2}\) or \(\mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{CXCH}_{3}\) or \(\mathrm{CH}_{3} \mathrm{CCH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}\) or \(\mathrm{NaCl}\) (d) CCCS \(\operatorname{cDT}\) CCC(O)CC

Compoends that contain an \(\mathrm{N}-\mathrm{H}\) group associate by hydrogen bonding- (a) Do you expect this associabion to be stronger or weaker than that of coupoxinds containing an \(\mathrm{O}-\mathrm{H}\) group? (b) Based on your answer to part (a), which would you predict to have the higher boiling point, 1-butanol or 1-butanamuine?

Draw the product of treating each alcohol with \(\mathrm{PCC}\). (a) M-Mexanol (b) 2.Mexanol (c) Cyclohexanol

IUPAC names of alcohols are derived by changing the suffix of the parent alkane from \(e\) to \(-\alpha\). \- The chain is numbered from the direction that gives the carbon bearing the - OH the lower number. \- In compounds containing other functional groups of higher precedence, the presence of - OH is indicated by the porefix hvdroxy-
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