Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'
(f)

Verified step by step guidance

1. Identify the functional group in the given molecule. The structure shows a tertiary alcohol group attached to a benzene ring.
2. Consider the reaction conditions (iii) SOCl₂, NEt₃. This is a common method for converting alcohols to alkyl chlorides via the formation of a chlorosulfite intermediate.
3. In the presence of SOCl₂ and NEt₃, the hydroxyl group (OH) of the tertiary alcohol will be replaced by a chlorine atom, resulting in the formation of a tertiary alkyl chloride.
4. Now consider the reaction conditions (iv) 1. TsCl, Et₃N 2. NaCN. The first step involves converting the alcohol to a tosylate, which is a good leaving group, using TsCl and Et₃N.
5. In the second step, the tosylate reacts with NaCN, leading to a nucleophilic substitution where the tosylate group is replaced by a cyano group (CN), forming a nitrile.

Key Concepts

Thionyl Chloride (SOCl₂) Reactivity

Thionyl chloride is a reagent commonly used for converting alcohols into alkyl chlorides. It reacts with alcohols to form the corresponding alkyl chloride and byproducts of sulfur dioxide and hydrochloric acid. Understanding this reaction mechanism is crucial for predicting the products when alcohols are treated with SOCl₂ in the presence of a base like NEt₃, which helps to neutralize the generated HCl.

TsCl and Base Reaction

TsCl, or tosyl chloride, is used to convert alcohols into tosylates, which are better leaving groups for subsequent nucleophilic substitutions. When combined with a base like Et₃N, the tosylate can then react with nucleophiles such as NaCN in a second step. This two-step process is essential for understanding how to predict the final products of the reaction sequence involving TsCl and NaCN.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution reactions, such as SN1 and SN2, are fundamental in organic chemistry for understanding how nucleophiles attack electrophiles. The choice of mechanism depends on factors like substrate structure and the nature of the nucleophile. Recognizing whether a reaction will proceed via SN1 or SN2 is vital for predicting the outcome of reactions involving alkyl halides and nucleophiles like NaCN.