SN1 rearrangement and neighbouring group participation in drawn substrates

14 questions on SN1 rearrangement and neighbouring group participation in drawn substrates from the Organic Reaction Mechanisms III: Nucleophilic Substitution chapter: 2 NEET level, 6 JEE Main, 6 JEE Advanced. Each one opens with its answer and solution.

• The secondary bromide shown is solvolysed in warm ethanol and gives a tertiary ether as a major product. Which carbocation is formed from the first-formed secon... NEET level, drawn structure
• The beta-chloro sulfide shown hydrolyses much faster than a primary alkyl chloride of similar size lacking the sulfur atom. What is the main reason? NEET level, drawn structure
• The primary bromide shown is warmed in ethanol in the presence of a weak nucleophile only (no strong base). The main substitution product has a rearranged carbo... JEE Main level, drawn structure
• The secondary alcohol shown is treated with concentrated HBr. The major bromide is obtained after rearrangement. Which structure is it? JEE Main level, drawn structure
• The trans-disubstituted sulfonate shown is heated in acetic acid (acetolysis) and compared with its cis isomer. Which statement is correct? JEE Main level, drawn structure
• The secondary bromide shown (configuration not specified) is hydrolysed in water by an S_N1 pathway, and its cation undergoes the favourable 1,2-methyl shift. I... JEE Advanced level, drawn structure
• The secondary bromide shown is warmed in aqueous ethanol containing silver nitrate. The cation undergoes successive 1,2-shifts to reach the most stable cation b... JEE Advanced level, drawn structure
• The bromohydrin shown (single stereoisomer) is treated with concentrated HBr. The reaction proceeds through the neighbouring bromine (bromonium ion) with overal... JEE Advanced level, drawn structure
• The (S)-configured alpha-bromo carboxylate shown is heated in very dilute aqueous base. Assume the carboxylate oxygen participates (neighbouring group participa... JEE Advanced level, drawn structure
• The beta-thio chloride shown (racemic) hydrolyses in water. Select all correct statements about the reaction. JEE Advanced level, drawn structure
• The primary bromide shown is solvolysed in hot ethanol with no strong nucleophile. Select all correct statements. JEE Main level, drawn structure
• The secondary bromide shown is solvolysed in warm aqueous ethanol. Select all correct statements about the cations and products. JEE Main level, drawn structure
• The mesylate shown carries a carbon-14 label (14C) at the carbon bearing the leaving group. It undergoes acetolysis entirely through a symmetrical bridged pheno... JEE Advanced level, drawn structure
• The secondary bromide shown is treated with aqueous silver nitrate. The cation first formed rearranges to a more stable one before capture by water. Which struc... JEE Main level, drawn structure