A compound A has the molecular formula CHBr.
When A is treated with sodium ethoxide in ethanol, the major product formed is B, which shows two distinct signals in the H NMR spectrum (excluding solvent and impurity peaks).
When A is reacted with silver nitrate in aqueous ethanol, a different product C is formed rapidly, and a precipitate is observed.
a) Propose a reasonable structure for compound A, justifying your answer using the given data.
b) Identify compounds B and C, giving full reaction mechanisms for their formation.
c) Explain why the reaction of A with sodium ethoxide proceeds via a different mechanism compared to its reaction with silver nitrate in aqueous ethanol.
d) Predict the outcome if A were reacted with potassium tert-butoxide in tert-butanol, and justify your answer with reference to steric and kinetic factors.
e) State and explain the effect of these reactions on the stereochemistry of the product(s), where applicable
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