Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.

g. 3,3-dimethyl-1-pentene + HBr

Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.

h. cis-2-butene + HBr

Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.

i. (Z)-2,3-dichloro-2-butene + H₂, Pd/C

Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.

j. (E)-2,3-dichloro-2-butene + H₂, Pd/C

Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.

k. (Z)-3,4-dimethyl-3-hexene + H₂, Pd/C

l. (E)-3,4-dimethyl-3-hexene + H₂, Pd/C

Of the possible products shown for the following reaction, are there any that will not be formed?

A, a compound with molecular formula C₆H₁₀, contains three methylene units. A reacts with one equivalent of H₂ over Pd/C to yield B. A reacts with aqueous acid to form a single product, C, and undergoes hydroboration/oxidation to form a pair of enantiomers, D and E. Ozonolysis of A followed by reaction with dimethyl sulfide forms F with molecular formula C₆H₁₀O₂. Provide structures for A–F.

The reaction of an alkene with diazomethane forms a cyclopropane ring. Propose a mechanism for the reaction. (Hint: It is a concerted reaction.)

Two chemists at Dupont found that ICH₂ZnI is better than diazomethane at converting a C=C bond to a cylcopropane ring. Propose a mechanism for the reaction, now known as the Simmons–Smith reaction in their honor.

Dichlorocarbene can also be generated by heating sodium trichloroacetate. Propose a mechanism for the reaction.

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?

a.

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?

b.

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?

c.

Draw the products of the following reactions, including their configurations:

Draw the products of the following reactions, including their configurations:

Draw the products of the following reactions, including their configurations:

a. Propose a mechanism for the following reaction:

b. Is the initially formed carbocation primary, secondary, or tertiary?

c. Is the rearranged carbocation primary, secondary, or tertiary?

d. Why does the rearrangement occur?

Which compound is hydrated more rapidly?

When the following compound is hydrated in the presence of acid, the unreacted alkene is found to have retained the deuterium atoms. What does this tell you about the mechanism for hydration?

When fumarate reacts with D₂O in the presence of the enzyme fumarase, only one isomer of the product is formed, as shown here. Is the enzyme catalyzing a syn or an anti addition of D₂O?

What stereoisomers are obtained when (S)-3-methyl-1-pentene reacts with Cl₂?

Propose a mechanism for the following reaction:

What hydrocarbon forms the following products after reaction first with ozone and then with dimethyl sulfide?

Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.

a.

Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.

b.