Question 1

Which of the following best describes the regiochemistry of HBr addition to 1,2-dimethylcyclohexene (as shown in $$image_1$$)?

Accepted Answer

The Br adds to the more substituted carbon due to Markovnikov's rule.

Question 2

What is the major product of the reaction between cyclopentene and HCl (see $$image_2$$)?

Accepted Answer

1-chlorocyclopentane

Question 3

In the addition of HBr to 1-cyclohexyl-1-propene ($$image_3$$), which product is favored and why?

Accepted Answer

The product with Br on the more substituted carbon, due to Markovnikov's rule.

Question 4

Which step in the mechanism of HCl addition to propene ($$image_4) $$involves the formation of a carbocation intermediate?

Accepted Answer

The initial attack of the alkene on HCl.

Question 5

When HBr is added to 2-methyl-2-butene, what is the stereochemical relationship between the products formed from addition to the top and bottom faces of the alkene (see $$image_5$$)?

Accepted Answer

They are enantiomers.

Question 6

For the addition of HBr to methylcyclohexene ($$image_6$$), what is the relationship between the products formed from addition to the top and bottom faces?

Accepted Answer

They are diastereomers.

Question 7

In the reaction of 2-methyl-2-butene with DBr ($$image_7$$), how many stereoisomers are possible and what is their relationship?

Accepted Answer

Four, consisting of two pairs of enantiomers (diastereomers).

Question 8

When 1,3-butadiene reacts with DCl ($$image_8$$), what is the expected outcome?

Accepted Answer

A mixture of products due to possible 1,2- and 1,4-addition.

Question 9

Why does the addition of HCl to 1-chlorocyclohexene ($$image_9) $$give almost exclusively anti addition of the two chlorines?

Accepted Answer

Because the intermediate carbocation is stabilized by the existing chlorine, favoring anti addition.

Question 10

In the reaction of a substituted cyclohexene with HBr ($$image_10$$), which product is favored and why?

Accepted Answer

The product with Br on the more substituted carbon, due to carbocation stability.

Question 11

Which of the following best explains Markovnikov's rule in the context of HX addition to alkenes?

Accepted Answer

The hydrogen atom adds to the carbon with the most hydrogens already attached.

Question 12

Which of the following is a possible reason for the formation of diastereomers in the addition of HBr to substituted cyclohexenes?

Accepted Answer

The formation of a new chiral center during the reaction.

Question 13

Which of the following statements about the addition of DCl to 1,3-butadiene is correct?

Accepted Answer

Both 1,2- and 1,4-addition products are possible.

Question 14

What is the expected product when HCl is added to propene, and what is the mechanism?

Accepted Answer

2-chloropropane via a carbocation intermediate.

Question 15

Which of the following best describes the stereochemistry of the addition of HBr to a planar alkene?

Accepted Answer

Both syn and anti addition can occur, leading to a mixture of stereoisomers.

Study Guide: Electrophilic Addition to Alkenes (Organic Chemistry)

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