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Chapter 4: Problem 132

Directions: This section contains multiple choice questions. Each question has 4 choices (a), (b), (c) and (d), out of which ONLY ONE is correct. Which of the following is the best method to convert 3-methylbut-1-ene to 3 -methyl butan-2-ol? (a) Acid catalyzed hydration. (b) Addition of con. \(\mathrm{H}_{2} \mathrm{SO}_{4}\) followed by hydrolysis. (c) Hydroboration-oxidation. (d) Oxymercuration-demercuration.

Short Answer

Expert verified
a) Acid-catalyzed hydration b) Addition of con. \(H_2SO_4\) followed by hydrolysis c) Hydroboration-oxidation d) Oxymercuration-demercuration Answer: d) Oxymercuration-demercuration

Step by step solution

01

Analyzing Acid Catalyzed Hydration Reaction

In the acid-catalyzed hydration reaction, the alkene reacts with water in the presence of an acid catalyst to form an alcohol. The reaction follows Markovnikov's rule, and the alcohol is added to the more substituted carbon in the alkene. If we apply this to the given substrate, 3-methylbut-1-ene, the product would be 2-methyl-but-2-ol, which is not the desired product.
02

Analyzing Addition of con. \(H_2SO_4\) followed by Hydrolysis Reaction

The addition of concentrated \(H_2SO_4\) and subsequent hydrolysis is another way to carry out hydration of alkenes. This reaction also follows Markovnikov's rule, and the formed product would still be 2-methyl-but-2-ol, which is not the desired product.
03

Analyzing Hydroboration-Oxidation Reaction

Hydroboration-oxidation is a two-step process that involves the addition of borane (BH3) to the alkene (Anti-Markovnikov), followed by the oxidation of the alkylborane intermediate with hydrogen peroxide (H2O2) under basic conditions, resulting in the formation of alcohol. Applying this reaction to the given substrate, 3-methylbut-1-ene, would result in the formation of 3-methyl-butan-1-ol, which is not the desired product.
04

Analyzing Oxymercuration-Demercuration Reaction

Oxymercuration-demercuration is a two-step reaction. In the first step, the alkene reacts with mercuric acetate (Hg(OAc)2) and water to form an organomercury intermediate. In the second step, the intermediate is treated with sodium borohydride (NaBH4) to form the alcohol product. This reaction also follows the Markovnikov's rule and does not produce carbocation rearrangements. The reaction will add an OH group to the second carbon of the alkene, forming the desired product, 3-methylbutan-2-ol.
05

Selecting the Correct Answer

Based on the analysis of each choice, the correct answer is (d) the Oxymercuration-demercuration reaction as it converts 3-methylbut-1-ene to the desired product, 3-methyl butan-2-ol.

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Most popular questions from this chapter

Oxidation of one mole of glycerol with periodic acid gives (a) 1 mole each of methanol, methanal and methanoic acid. (b) 1 mole of methanal and 2 moles of methanoic acid. (c) 1 mole of methanoic acid and 2 moles of methanal. (d) three moles of methanal.

An organic compound (x) was heated with \(\mathrm{NaOH}\) solution and then acidified with dilute \(\mathrm{HNO}_{3} \cdot\) Addition of silver nitrate solution gave a white precipitate completely soluble in ammonium hydroxide. The compound (x) is (a) \(\mathrm{p}\) -chlorotoluene (b) vinyl chloride (c) \(\mathrm{p}\) - dichlorobenzene (d) benzyl chloride

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