The structures of the compounds A and B are to be suggested on the basis of the given observations, and the relationship between them is to be determined. Concept introduction: Alkene undergoes hydroboration-oxidation reaction which results in the formation of alcohol. It is a two-step reaction, which takes place with a regioselectivity opposite to the Markovnikov’s rule. A hydrogen and hydroxyl group are added to the double bonded carbon atoms in a syn manner. The hydrogen adds to the more substituted carbon atom while the hydroxyl gets attached to a less substituted carbon atom. There are no carbocations formed, and hence no rearrangements take place. Enantiomers are mirror images. They have opposite configuration at each chiral center. Diastereomers have the same configuration at one chiral center and opposite configuration at the other chiral center.

Question

Want to see the full answer?

Answer 1

Question

Chapter 12, Problem 60P

Interpretation Introduction

Interpretation:

The structures of the compounds A and B are to be suggested on the basis of the given observations, and the relationship between them is to be determined.

Concept introduction:

Alkene undergoes hydroboration-oxidation reaction which results in the formation of alcohol.

It is a two-step reaction, which takes place with a regioselectivity opposite to the Markovnikov’s rule.

A hydrogen and hydroxyl group are added to the double bonded carbon atoms in a syn manner.

The hydrogen adds to the more substituted carbon atom while the hydroxyl gets attached to a less substituted carbon atom. There are no carbocations formed, and hence no rearrangements take place.

Enantiomers are mirror images. They have opposite configuration at each chiral center.

Diastereomers have the same configuration at one chiral center and opposite configuration at the other chiral center.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

On being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) yielded a mixture of two alkenes B and C, each having the molecular formula C7H14. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3-ethylpentane. Suggest structures for compounds A, B, and C consistent with these observations.

(S)-2-butanol reacts with potassium dichromate (K2CrO4) in aqueous sulfuric acid to give A(C,HgO). Treatment of A with ethylmagnesium bromide in anhydrous ether gives B(C,H140). Draw the structure of B.

Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr) which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (Ch3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which reacts with 2 equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and Pt catalyst to give 2-methylpropylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.