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Chapter 10: Q.19. (page 404)

Question: Draw the products, including stereochemistry, of each reaction. 

Short Answer

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Answer

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01

Formation of carbocation

The pi-electron density is transferred to the hydrogen atom from the HX molecule, leading to pi-bond cleavage and carbocation formation.

02

Stereochemistry

First, the hydrogen atom is added to the carbon with more hydrogen atoms or the less substituted carbon.

If the pre-existing group on C=C is outside the plane of the molecule, then hydrogen is added from the opposite side of the group.

However, if the group is in the plane, the hydrogen atom is added from either above or below the plane. The pre-existing group is moved to the other side of the plane.

03

Products of the given reactions

a. The hydrogen atom is added to the less substituted carbon as per Markovnikov’s rule. The chloride ion Cl-attacks the 3°carbocation to form two enantiomers.

Products of a

b. The hydrogen atom is added to the less substituted carbon as per Markovnikov’s rule. The chloride ion Cl-attacks the 2°carbocation to form two diastereomers.


Products of b

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Most popular questions from this chapter

Question: Draw the constitutional isomer formed when the following alkenes are treated with each set of reagents: [1] H2O,H2SO4; or [2] BH3followed by H2O2,HO-.

Question: What three alkenes (excluding stereoisomers) can be used to prepare 3-chloro-3-methylhexane by addition of HCl?

Question: Draw a stepwise mechanism for the following reaction.

Question: Calculate the number of degrees of unsaturation for each molecular formula.

a. C6H8

b. C40H56

c. C10H16O2

d. C8H9Br

e. C8H9ClO

f. C7H11N

g. C4H8BrN

h. C10H10ClNO

Question: Treatment of 3-methylcyclohexene with HCl yields two products, 1-chloro-3-methylcyclohexane and 1-chloro-1-methylcyclohexane. Draw a mechanism to explain this result.
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