Give the substitution products expected from solvolysis of each compound by heating in ethanol.
(c)
(d)

Verified step by step guidance

1. Step 1: Identify the type of halide in each compound. Both compounds contain a bromine atom attached to a carbon atom. In compound (c), bromine is attached to a secondary carbon, while in compound (d), bromine is attached to a tertiary carbon.
2. Step 2: Recognize the reaction conditions. Solvolysis in ethanol typically proceeds via an SN1 mechanism, especially for secondary and tertiary alkyl halides. This involves the formation of a carbocation intermediate after the departure of the bromide ion.
3. Step 3: Analyze the stability of the carbocation intermediates. In compound (c), the secondary carbocation formed is moderately stable. In compound (d), the tertiary carbocation formed is highly stable due to hyperconjugation and inductive effects from the surrounding alkyl groups.
4. Step 4: Predict the substitution product. Ethanol acts as the nucleophile in this reaction. After the carbocation is formed, ethanol will attack the positively charged carbon, leading to the formation of an ethyl ether product (R-OCH2CH3).
5. Step 5: Consider any potential rearrangements. For compound (c), no rearrangement is expected as the secondary carbocation is relatively stable. For compound (d), no rearrangement is needed as the tertiary carbocation is already highly stable.

Key Concepts

Solvolysis

Solvolysis is a type of nucleophilic substitution reaction where a solvent acts as a nucleophile. In organic chemistry, this often involves the reaction of an alkyl halide with a solvent like ethanol, leading to the formation of substitution products. The reaction typically proceeds through either an SN1 or SN2 mechanism, depending on the structure of the substrate and the conditions of the reaction.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution can occur via two primary mechanisms: SN1 and SN2. The SN1 mechanism involves a two-step process where the leaving group departs first, forming a carbocation intermediate, followed by nucleophilic attack. In contrast, the SN2 mechanism is a one-step process where the nucleophile attacks the substrate simultaneously as the leaving group departs, leading to an inversion of configuration at the carbon center.

Ethanol as a Solvent

Ethanol is a polar protic solvent that can stabilize ions and facilitate nucleophilic substitution reactions. Its ability to donate hydrogen bonds makes it effective in solvolysis, as it can stabilize the carbocation formed in SN1 reactions or assist in the nucleophilic attack in SN2 reactions. The choice of solvent can significantly influence the reaction pathway and the products formed.