Alkenes needed for the formation of given compounds by the hydroboration–oxidation reaction are to be provided. Concept introduction: Alkenes are converted to alcohols by methods, such as acid-catalyzed hydration of alkenes, oxymercuration–demercuration reactions, and hydroboration–oxidation reactions. Hydroboration–oxidation reaction proceeds by anti-Markovnikov’s regioselectivity. Anti-Markovnikov addition is an addition reaction between an electrophile compound HX and either an alkene or alkyne where the hydrogen atom of HX bonds to the carbon atom with the least number of hydrogen atoms in the initial alkene double bond or alkyne triple bond and the X bonds to the other carbon atom.

Question

Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (a) Hydrogen chloride (b) Dilute sulfuric acid (c) Diborane in diglyme, followed by basic hydrogen peroxide (d) Bromine in carbon tetrachloride (e) Bromine in water (f) Peroxyacetic acid (g) Ozone (h) Product of part (g) treated with zinc and water (i) Product of part (g) treated with dimethyl sulfide (CH3)2S

Answer 1

Question

Chapter 11, Problem 28P

Interpretation Introduction

Interpretation:

Alkenes needed for the formation of given compounds by the hydroboration–oxidation reaction are to be provided.

Concept introduction:

Alkenes are converted to alcohols by methods, such as acid-catalyzed hydration of alkenes, oxymercuration–demercuration reactions, and hydroboration–oxidation reactions.

Hydroboration–oxidation reaction proceeds by anti-Markovnikov’s regioselectivity.

Anti-Markovnikov addition is an addition reaction between an electrophile compound HX and either an alkene or alkyne where the hydrogen atom of HX bonds to the carbon atom with the least number of hydrogen atoms in the initial alkene double bond or alkyne triple bond and the X bonds to the other carbon atom.

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