Draw the major products of the reactions below.

Give the major products formed from the reaction of cis-3-methylcyclopentanol with each of the following reagents. Include stereochemistry.

(a) PCl₃

(b) SOCl₂

(c) Lucas reagent

What are the best ways (alkoxide ion and alkyl halide pairs) to synthesize the following ethers?

Predict the product of the given reaction.

Acid-catalyzed condensation is impractical for the synthesis of the unsymmetrical ether shown below. Explain why this is true.
isopropyl propyl ether, (CH₃)₂CH−O−CH₂CH₂CH₃

What are the electrophile and the nucleophile in the first step of the reaction mechanism?

Provide the synthetic steps needed to produce trans-2,3-epoxyhexane from hexan-2-ol in good yield. You may use additional reagents as needed

Identify the product of the reaction shown below:

Consider the following general scheme:

How does benzyl ether protect the 1° alcohol? What are the reagents used in the first step? 

How would you synthesize the following compound using organic molecules with no more than three carbons? Hint: A protecting group will be required for the synthesis.

Which alkene reacts with Ti(OiPr)₄, (+)-diethyltartrate, and t-butylhydroperoxide to form a nonracemic mixture of the given epoxide?

The foul smell excreted by skunks is due to a number of thiols. Show how you would synthesize the following thiol using vinylcyclohexane?

The compound ClCH₂CH₂SCH₃ has the ability to alkylate amino groups on enzymes (enzyme−NH₂), making the enzymes inactive.

(i) Propose a mechanism to explain the alkylation reaction.

(ii) Bleach (NaOCl) can inactivate or oxidize ClCH₂CH₂SCH₃. Predict the product/s of the oxidation reaction.

Identify the oxidation number of the specified carbon in the molecule.

Deuterium-containing compounds (D = ²H) are helpful for kinetic and metabolic research with novel drugs. LiAlD₄, reagent LiAlH₄'s counterpart in reactivity, is one approach to introduce deuterium. Using LiAlD₄ and D₂O as your sources of deuterium and other non-deuterated starting materials you choose, demonstrate how to create this deuterium-labeled molecule, CH₃CH₂CD₂OH.

Determine whether the below-given species is a strong, intermediate, or weak nucleophile. Would this nucleophile add directly to a carbonyl or wait for the carbocation formation before adding to the carbonyl?

Draw the compound generated when the following Grignard reagent preparation is done in the presence of heavy water (D₂O).

A range of organometallic compounds, known for their strong nucleophilic properties, can undergo reactions with epoxides. Determine the product of the reaction below. (Note: In the first step, assume that the C–Mg bond is ionic, such that carbon has a negative charge.)

Write a synthetic route showing how you would transform 2-chlorocyclopentanol into the diol shown below:

Use any additional reagents as required.

Identify the major product of the given reaction sequences.

Show how would you convert the following compound into the given product.

Propose a synthesis for the transformation below. Use whatever additional reagents that are needed.

Show how you would synthesize each of the following compounds using cyclopentane as your starting material.
(a) 3-bromocyclopent-1-ene
(b) cyclopenta-1,3-diene
(c) cyclopentanol

Provide the missing products, in each step of the given synthesis. Include any important stereochemistry.