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Chapter 10: Q.19. (page 404)

Question: Draw鈥倀he鈥俻roducts,鈥俰ncluding鈥俿tereochemistry,鈥俹f鈥俥ach鈥俽eaction.鈥�

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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鈥檚 rule. The chloride ion Cl-attacks the 3掳carbocation to form two enantiomers.

Products of a

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


Products of b

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Most popular questions from this chapter

Question: What product is formed when each alkene is treated with HCl?

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

Question: Rank the following isomers in order of increasing boiling point.

Question: Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms 伪-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl , forms a constitutional isomer, 伪-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile鈥攁 carbocation鈥� to a double bond.

Question: Draw a stepwise mechanism for the following reaction. Draw the transition state for each step.
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