$$1.\ O_3$,\ -78^\circ C \\ 2.\ (CH_3$)_2S$$

Question 1

Which product is formed when cyclohexylpropene (first image) reacts with Br$$_2 in H$_2O$$?

Accepted Answer

A bromohydrin with Br and OH added anti to each other across the double bond, with Br on the more substituted carbon.

Question 2

What is the major product when 2-methyl-2-pentene (fourth image) undergoes acid-catalyzed hydration (H$$_2SO$_4$$, H$$_2O$$)?

Accepted Answer

2-methyl-2-pentanol

Question 3

Which reagent would convert cyclohexylpropene (first image) to a cyclohexylpropanal (aldehyde)?

Accepted Answer

$$1.\ O_3$,\ -78^\circ C \ 2.\ (CH_3$)_2S$$

Question 4

Which product is formed when 2-methylcyclohexene (sixth image) reacts with HBr?

Accepted Answer

1-bromo-2-methylcyclohexane (see image 11)

Question 5

Which mechanism best explains the formation of a bromohydrin from an alkene and Br$$_2 in H$_2O$$?

Accepted Answer

Formation of a bromonium ion intermediate, followed by nucleophilic attack by water.

Question 6

What is the stereochemical outcome when 2-methylcyclohexene reacts with Br$$_2 in CH$_2Cl$_2$$?

Accepted Answer

Trans-1,2-dibromo-2-methylcyclohexane (see image 21)

Question 7

Which product is formed when 3-methyl-2-pentene (second image) undergoes hydroboration-oxidation?

Accepted Answer

3-methyl-2-pentanol (see image 8)

Question 8

Which statement best explains the regioselectivity of hydroboration-oxidation of propene?

Accepted Answer

The boron adds to the less substituted carbon, and the hydride adds to the more substituted carbon.

Question 9

Which product is formed when 2-methylcyclohexene reacts with mCPBA?

Accepted Answer

2-methylcyclohexene oxide (epoxide, see image 17)

Question 10

Which product is formed when 2-methylcyclohexene reacts with H$$_2SO$_4$$ and H$$_2O$$?

Accepted Answer

2-methylcyclohexanol (see image 12)

Question 11

Which product is formed when 2-methylcyclohexene reacts with O$$_3$$ followed by (CH$$_3$$)$$_2S$$?

Accepted Answer

2-methylcyclohexanone (see image 14)

Question 12

Which product is formed when 2-methylcyclohexene reacts with Br$$_2 in H$_2O$$?

Accepted Answer

Trans-2-bromo-1-hydroxy-2-methylcyclohexane (see image 13)

Question 13

Which product is formed when 2-methylcyclohexene reacts with HBr?

Accepted Answer

1-bromo-2-methylcyclohexane (see image 11)

Question 14

Which product is formed when 2-methylcyclohexene reacts with Br$$_2 in CH$_2Cl$_2$$?

Accepted Answer

Trans-1,2-dibromo-2-methylcyclohexane (see image 21)

Question 15

Which product is formed when 2-methylcyclohexene reacts with mCPBA?

Accepted Answer

2-methylcyclohexene oxide (epoxide, see image 17)

Question 16

Which product is formed when 2-methylcyclohexene reacts with O$$_3$$ followed by (CH$$_3$$)$$_2S$$?

Accepted Answer

2-methylcyclohexanone (see image 14)

Question 17

Which product is formed when 2-methylcyclohexene reacts with Br$$_2 in H$_2O$$?

Accepted Answer

Trans-2-bromo-1-hydroxy-2-methylcyclohexane (see image 13)

Question 18

Which product is formed when 2-methylcyclohexene reacts with HBr?

Accepted Answer

1-bromo-2-methylcyclohexane (see image 11)

Predicting Products of Alkene Reactions in Organic Chemistry

Study Guide - Practice Questions