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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: How many degrees of unsaturation are present in each compound?

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Question: (a) Draw all possible stereoisomers of 4-methylnon-2-ene, and name each isomer, including its E, Z and R, S prefixes. (b) Label two pairs of enantiomers. (c) Label four pairs of diastereomers.

Question: What two alkenes give rise to each alcohol as the major product of acid-catalyzed hydration?

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: Addition of HBr to which of the following alkenes will lead to a rearrangement?
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