What is the major product(s) of each of the following reactions?
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Verified step by step guidance

1. Step 1: Analyze the starting material. The molecule is a cyclopentanol derivative with a hydroxyl (-OH) group and a methyl group attached to the ring. The hydroxyl group is in the axial position.
2. Step 2: Understand the role of TsCl/pyridine. Tosyl chloride (TsCl) reacts with the hydroxyl group in the presence of pyridine to convert it into a tosylate (-OTs) group. This step makes the hydroxyl group a better leaving group.
3. Step 3: Consider the stereochemistry of the tosylation reaction. The tosylate group will retain the stereochemistry of the original hydroxyl group, as this reaction does not invert the configuration.
4. Step 4: Examine the second reagent, NaCN. Sodium cyanide (NaCN) is a nucleophile that will perform an SN2 reaction, displacing the tosylate group. Since SN2 reactions proceed with inversion of configuration, the cyanide group (-CN) will attach to the carbon in the equatorial position.
5. Step 5: Predict the major product. The major product will be a cyclopentane ring with a cyanide group (-CN) in the equatorial position and a methyl group in the axial position, due to the stereochemical inversion during the SN2 reaction.

Key Concepts

Alcohol Activation

In organic chemistry, alcohols can be converted into better leaving groups through activation. In this reaction, TsCl (tosyl chloride) is used in the presence of pyridine to convert the alcohol (-OH) into a tosylate, which is a more reactive species. This transformation facilitates subsequent nucleophilic substitution reactions.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, after the alcohol is converted to a tosylate, NaCN (sodium cyanide) acts as the nucleophile, attacking the carbon atom bonded to the tosylate and resulting in the formation of a nitrile (R-C≡N).

Formation of Nitriles

Nitriles are organic compounds containing a cyano group (-C≡N) and are often formed through nucleophilic substitution reactions involving alkyl halides or activated alcohols. The reaction of the tosylate with NaCN leads to the formation of a nitrile, which can be useful in various synthetic applications, including the synthesis of amines and carboxylic acids.