Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.
g. 1−bromo−1−methylcyclopentane + NaOEt in ethanol

Verified step by step guidance

1. Step 1: Analyze the reactants. The starting material is 1-bromo-1-methylcyclopentane, which is a secondary alkyl halide. The reagent is sodium ethoxide (NaOEt) in ethanol, which is a strong base and a good nucleophile.
2. Step 2: Consider the possible reaction mechanisms. Since the substrate is a secondary alkyl halide and the reagent is a strong base, the reaction is likely to proceed via an E2 elimination mechanism rather than substitution (SN2 or SN1). This is because strong bases favor elimination, especially with secondary substrates.
3. Step 3: Identify the β-hydrogens available for elimination. In the cyclopentane ring, there are β-hydrogens on the carbons adjacent to the carbon bonded to the bromine. These hydrogens can be abstracted by the ethoxide ion during the elimination process.
4. Step 4: Predict the product(s). The elimination of HBr will result in the formation of a double bond in the cyclopentane ring. The most stable alkene product will be formed, following Zaitsev's rule, which states that the more substituted alkene is favored.
5. Step 5: Explain the stereochemistry and regioselectivity. The elimination reaction will proceed in an anti-periplanar fashion, meaning the β-hydrogen and the leaving group (Br) must be in opposite planes. This stereochemical requirement will influence the formation of the product. Additionally, the major product will be the more substituted alkene due to its greater stability.

Key Concepts

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, NaOEt acts as a nucleophile, attacking the carbon atom bonded to the bromine in 1-bromo-1-methylcyclopentane. The mechanism can proceed via either an SN1 or SN2 pathway, depending on the substrate structure and reaction conditions.

Elimination Reactions

Elimination reactions involve the removal of a small molecule (like HBr) from a larger molecule, resulting in the formation of a double bond. In the presence of a strong base like NaOEt, the reaction can favor elimination over substitution, leading to the formation of alkenes. The mechanism can be E1 or E2, with E2 being more likely in this case due to the strong base and steric hindrance.

Regioselectivity and Stereoselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others, while stereoselectivity involves the preference for one stereoisomer over another. In the reaction of 1-bromo-1-methylcyclopentane with NaOEt, the formation of products will depend on the stability of the resulting alkenes and the steric factors influencing the elimination pathway, which can lead to different regio- and stereoisomeric products.