Exam 4: Reactions of Alkenes and Alkynes

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

The following reaction is carried out in cyclohexane with the application of heat. Write the complete equation for the reaction below. If more than one major organic product is expected, draw each one.

Povidone is produced commercially as a series of products having mean molecular weights ranging from about 10,000 to 700,000. Complexed with iodine, povidone yields an iodophor, marketed under the tradename Betadine, which is used as a topical anti-infective. Identify the monomer unit(s) in povidone.

Instructions: Predict the structure of the alkene you would use to prepare the folloiwng compounds. There may be more than one answer in some cases. -Predict.

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

Draw two resonance structures for the species below.

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant. -Predict and indicate.

MATCH each definition to the term it describes. Place the letter of the term in the blank to the left of the definition. -Refer to Instructions. _____Predicts that in electrophilic additions to alkenes the more stable carbocation intermediate is formed.

What was the other product formed in the KMnO₄ oxidation of B?

MATCH each definition to the term it describes. Place the letter of the term in the blank to the left of the definition. -Refer to Instructions. _____Assigns priorities to substituent groups on a carbon.

To answer the questions below, consider the following information: In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the label "Compound A: C₇H₁₂. Government agents have offered you a considerable sum to determine the structure of this compound. After verifying the molecular formula by elemental analysis, you find that Compound A reacts with 1 mol equiv of hydrogen and, after treatment with acidic KMnO₄, gives the dicarboxylic acid C (see below). Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with 1 mol equiv of hydrogen, but yields cyclohexanone after treatment with acidic KMnO₄. -Refer to Instructions. Suggest structures for A and B.

Rank the carbocations below in order of increasing stability (least stable = 1; most stable = 3). Place the number corresponding to the carbocation's relative stability in the blank below the structure.

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant. -Predict and indicate.

On the structures provided, draw arrows showing the electron flow in the reaction mechanism for the electrophilic addition of hydrogen bromide to hex-1-yne.

Instructions: Predict the structure of the alkene you would use to prepare the folloiwng compounds. There may be more than one answer in some cases. -Predict.

Instructions: Predict the structure of the alkene you would use to prepare the folloiwng compounds. There may be more than one answer in some cases. -Predict.

Instructions: 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?

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant. -Predict and indicate.

Draw all the isomeric products formed from the addition of HCl to the following compound.

Instructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant. -Predict and indicate: