Draw the plausible mechanism that explains the given reaction.

(i) Draw the alkene molecule needed to produce the following compound:

(ii) Draw any other epoxide formed in the reaction.

(iii) Assign the R and S configuration to each chiral center.

Write suitable reagents for the given reaction.

What is the major product of the reaction between 1-ethylcyclopent-1-ene and cold dilute KMnO₄ solution (pH > 8)?

When an unknown compound was allowed to react with ozone, followed by dimethyl sulfide and a small amount of water, it produced acetic acid, 3-methylbutan-2-one, and 3-oxopenatanoic acid. Determine the structure of the unknown compound. Which information can not be determined with this reaction?

For the reaction shown, draw the mechanism.

Draw the structure of the product expected when the molecule below reacts with an excess of hot, concentrated potassium permanganate.

Provide the product(s) obtained when cycloheptyne reacts with the following reagents:

(i) KMnO₄, H₂O, neutral

(ii) KMnO₄, KOH, H₂O, heat, then H⁺, H₂O

Draw the products of each of the reactions between 3-heptyne and the reagents below.

i. HCl (1 mol)

ii. HCl (2 mol)

Determine the identity of products obtained in the reaction of but-1-yne with each of the reagents shown below.
(i) H₂, Pd/BaSO₄ catalyst, quinoline
(ii) Br₂ (1 equivalent)
(iii) Br₂ (2 equivalents)

Oxymercuration-reduction is an excellent method for obtaining single compounds from the hydration of symmetrical internal or terminal alkynes. Draw the product of the oxymercuration-reduction reaction for the following compound:

1-pentyne

Show how the following synthetic transformation can be accomplished. Give the structures of all intermediates.

trans-but-2-ene → cis-but-2-ene

Show how the following compound can be prepared, starting with cyclopentane.

Determine which of the following radicals is the most stable, and thus, is most likely to be produced from an ether.

Determine the number of alkyl chlorides expected from the monochlorination of the alkane given below. Do not include stereoisomers.

What monobrominated derivatives can be synthesized as major products using the free-radical bromination for each alkane?

(i) cyclohexane

(ii) methylcyclohexane

Assuming that the desired product for each reaction is the tertiary alkyl halide: i. What is the effective mass yield (EMY) for each reaction? ii. Which reaction would you consider greener? Explain.

Draw the major alkyl halide product(s) formed in the reaction below with 1 eq. of HBr. Note: Ignore stereochemistry.

The reaction of 1,2-dimethylcyclohexene with NBS under UV light produces a mixture of two products.

However, the reaction of cyclopentene with NBS only produces one product despite the generation of a resonance-stabilized radical. Explain why this reaction does not yield a second product.

Show how the following compound can be synthesized using free-radical halogenation. Explain why only one major product is expected. (Ignore stereochemistry.)

Determine which alcohol in the given pair is more acidic. Explain your choice.

2-propanol and 2-propanethiol

Most ethers are generally considered to be very unreactive. They are unreactive towards most bases and only react with very strong bases where they undergo cleavage of the ether bond. Ethers, however, form peroxides when stored with oxygen for long periods. For example, a bottle of ether once opened will be filled with air and over time the oxygen can convert a small amount of ether to ether peroxide. Ether peroxides are very unstable and can explode at slight heating. To overcome this problem, old ether solvents are always refluxed with sodium metal (a very strong reducing agent) to convert the ether peroxides to alkoxides before they are distilled.
A grad student was refluxing THF (tetrahydrofuran) with sodium metal and a small amount of benzophenone. After a couple of hours, all of the ether in the distillation flask turned dark purple. Is there an explanation for this change in color?

Draw the structure consistent with the name 3,4-epoxy-2-methylheptane.

Provide the structure of the compound with a name (1S,5S)-5-ethylcyclohex-2-enethiol.

Give a reagent and an alkene reactant required to produce the alcohol shown below.

In converting alcohol into a good leaving group, the hydroxy (-OH) group is protonated. Propose the mechanism for the given reaction.

The following coordinate diagram for the nucleophilic displacement of hydroxide shows that the reaction is unfavorable. Draw a curve demonstrating that the substitution reaction is favorable when tosylate is used.