Question 1

Which of the following best describes the E/Z configuration of the following alkene?

$$\mathrm{CH_3CH=CHCH_2CH_2OH}

A. $$Assign priorities to the groups attached to each alkene carbon and determine the configuration.

Accepted Answer

E, because the highest priority groups on each carbon are on opposite sides of the double bond.

Question 2

Given the IUPAC name 3-ethyl-2,2-dimethyl-3-heptene, which of the following is the correct condensed structural formula?

Accepted Answer

$$\mathrm{CH_3CH_2C(CH_3$)_2CH=CHCH_2CH_3}$$

Question 3

Which of the following alkenes is more stable and why?

A. 3-ethyl-2,2-dimethyl-3-heptene
B. 4-methyl-1-pentene

Accepted Answer

A, because it is more substituted.

Question 4

What is the correct IUPAC name for the following molecule?

$$\mathrm{CH_2$=CHCH_2CHBrCH_3}$$

Accepted Answer

4-bromopent-1-ene

Question 5

Which of the following compounds will be most reactive toward HBr addition and why?

A. butane
B. 1-butene
C. 2-butene
D. 2-methyl-1-propene

Accepted Answer

D, because it forms the most stable carbocation intermediate.

Question 6

What is the major product of the hydroboration-oxidation of 1-hexene ($$\mathrm{CH_2$=CH(CH_2$)_3CH_3}$$)?

Reagents: $$1)\ \mathrm{B_2H_6,\ diglyme}\ 2)\ \mathrm{H_2O_2,\ NaOH}$$

Accepted Answer

$$\mathrm{CH_3$(CH_2$)_4CH_2OH}$$

Question 7

Ozonolysis of 2-butene ($$\mathrm{CH_3CH=$$CHCH_3$$}) $$followed by reduction with Zn/H$$_2O $$yields which of the following products?

Accepted Answer

Two molecules of acetaldehyde ($$\mathrm{CH_3CHO})$$

Question 8

Which of the following best describes the product of the reaction of cyclohexene with MCPBA?

Accepted Answer

Cyclohexene oxide (an epoxide)

Question 9

When 1-butene reacts with HBr in the presence of peroxides ($$\mathrm{H_2O_2}$$), what is the major product?

Accepted Answer

1-bromobutane (anti-Markovnikov addition)

Question 10

What is the major product when 2-methylpropene reacts with HCl (1 equivalent)?

Accepted Answer

tert-Butyl chloride ($$\mathrm{(CH_3$)_3CCl})$$

Question 11

What is the product of the reaction of 1-hexene with Br$$_2 in $$CCl$$_4$$?

Accepted Answer

1,2-dibromohexane (anti addition)

Question 12

Which of the following best describes the mechanism of acid-catalyzed hydration of alkenes (e.g., 1-butene with $$\mathrm{H_2O/H_2SO_4}$$)?

Accepted Answer

Markovnikov addition of water via a carbocation intermediate

Question 13

Which of the following is the major product when 2-butene reacts with HBr in CCl$$_4$$?

Accepted Answer

2-bromobutane

Question 14

A patient is exposed to ozone in the atmosphere, which reacts with the double bonds in unsaturated fatty acids in their body. What type of products are formed from the ozonolysis of these double bonds?

Accepted Answer

Aldehydes and/or ketones

Question 15

Which of the following statements about the reactivity of alkenes toward electrophilic addition is correct?

Accepted Answer

Alkenes with more alkyl substitution are generally more reactive due to greater carbocation stability.

Question 16

Which of the following best explains why anti-Markovnikov addition occurs in the presence of peroxides during HBr addition to alkenes?

Accepted Answer

A radical mechanism is favored, leading to bromine adding to the less substituted carbon.

Question 17

Which of the following is the correct product for the syn dihydroxylation of cyclohexene?

Accepted Answer

cis-1,2-cyclohexanediol

Question 18

A chemist treats 1-pentene with $$\mathrm{H_2O/H_2SO_4}. $$What is the major product?

Accepted Answer

2-pentanol (Markovnikov addition)

Question 19

Which of the following best describes the stereochemistry of the addition of Br$$_2 to $$cyclopentene in CCl$$_4$$?

Accepted Answer

Anti addition, leading to trans-1,2-dibromocyclopentane

Organic Chemistry Quiz 6 Study Guidance

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