8.19: Additional Exercises

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Addition of Hydrogen Halides to Alkenes

9-1 Give the IUPAC name for the product of the following reaction.

9-2 Draw the reaction mechanism of the previous problem (9-1).

9-3 Identify the product of the following reactions.

9-4 Identify the products of the following reactions.

Addition of Water: Hydration of Alkenes

9-5 Identify the product of the following reactions.

9-6 Identify the product of the following reaction.

9-7 Propose a plausible route of synthesis for the following product starting with 1-butanol.

9-8 Which of the following alkenes can be used to obtain 3,4-dimethylpentan-2-ol through a hydration reaction using dilute acid?

a) (2Z)-3,4-dimethylpent-2-ene

b) 3,4-dimethylpent-1-ene

c) 2,3,4-trimethylpent-2-ene

d) 2,4-dimethyl-3-methylidenepentane

Hydration by Oxymercuration-Demercuration

9-9 Explain why hydration of an alkene by Oxymercuration-Demercuration gives the Markovnikov product.

9-10 Identify the products of the following reactions.

9-11 Identify the product of the following reaction.

9-12 Propose a possible route of synthesis for the following ether starting with 2-ethylbutan-1-ol.

9-13 Give the IUPAC name of the product of the following reaction.

a) 2-methylpropan-2-ol

b) 2,2-dimethylbutane

c) 2-methoxy-2-methylpropane

d) 1,1-dimethylcyclopropane

Hydroboration of Alkenes

9-14 Identify the products of the following reactions.

9-15 Identify the products of the following reactions.

9-16 Give the IUPAC name for the product of the following reaction.

Addition of Halogens to Alkenes

9-17 Identify the products of the following reactions.

9-18 Identify the product of the following reaction.

9-19 What is the product of the following reaction?

a) (2Z)-2-bromo-3-methylpent-2-ene

b) 2-bromo-3-methylpentane

c) 2,3-dibromo-3-methylpentane

d) (2E)-4-bromo-3-methylpent-2-ene

9-20 What reagents can be used in each step to obtain the following products?

9-21 Explain why you do not obtain a mixture of cis- and trans-brominated products when you react Br2/CCl4 with cyclopentene.

Formation of Halohydrins

9-22 Identify the product of the following reaction, making sure to include stereochemistry.

9-23 Draw the mechanism of the reaction in the previous problem (9-22).

9-24 Give the IUPAC name for the product of the following reaction.

9-25 Identify the product of the following reaction.

Catalytic Hydrogenation of Alkenes

9-26 Identify the products of the following reactions.

9-27 Suggest a possible route of synthesis, that includes a catalytic hydrogenation step, to obtain the following product.

9-28 Identify the product of the following reaction.

9-29 Identify the product of the following reaction, making sure to include stereochemistry.

Addition of Carbenes to Alkenes

9-30 Identify the product of the following reaction.

9-31 Identify the product(s) of the following reaction.

9-32 Identify the product of the reaction when (2E)-3-methylhex-2-ene reacts with the carbene product from the previous problem (9-31), then reacts with Br₂ and hv.