Exam 8: Reactions of Alkenes and Alkynes

Predict the product of the reaction below. Indicate regiochemistry and stereochemistry if relevant. (D₂ = deuterium)

The reaction of 2-methylpropene with HBr in ether gives one of the two products below. Answer the following question(s) about this reaction. -Refer to instructions. The reaction mixture would contain a majority of which isomeric product?

The reaction of 2-methylpropene with HBr in ether gives one of the two products below. Answer the following question(s) about this reaction. -Refer to instructions. Which product would have a lower energy transition state for the formation of the intermediate leading to it?

The reaction conditions to carry out the production of cyclopentene using bromocyclopentane as the starting material would be:

What type of reactive intermediate is formed in the reaction of an alkene with aqueous acid to give an alcohol?

What is the major organic product obtained from the following reaction?

For each reaction below, suggest structures for alkenes that give the indicated reaction products. There may be more than one answer. -Suggest structure(s):

What is the best choice of reagents to perform the following transformation?

What type of reaction mechanism accounts for the reaction of an alkyne with HBr to give an alkyl bromide?

Which set of reagents is used for the Markovnikov addition of water to an alkene without rearrangement?

Complete the following reaction

Consider the reaction below to answer the following question(s). Alkenes may be hydrated by the hydroboration/oxidation procedure shown. -Refer to instructions. The intermediate formed in the first step of this reaction is:

Predict the structure of the alkene you would use to prepare the alkyl halide below. -Predict:

To answer the question(s) below, consider the following reaction: When cyclohexene reacts with chlorine in tetrachloromethane, the trans-dihalide is formed. -Refer to instructions. Write the complete, stepwise mechanism for this reaction. Show all intermediate structures and all electron flow using arrows.

What is the major product of this reaction?

Circle whichever of the following would be classified as a conjugated diene.

Draw the structure of the polymer formed from the monomer given below, showing four repeating units.

Compare the products when the following compound reacts with Br₂ in the presence of an organic solvent versus water.

The product(s) of the reaction when carried out in an organic solvent would be:

The reaction of 2-methylpropene with HBr in ether gives one of the two products below. Answer the following question(s) about this reaction. -Refer to instructions. Which product is the Markovnikov product?