Treatment of an alkyl halide with AgNO₃ in alcohol often promotes ionization.
Ag⁺ + R–Cl → AgCl + R⁺
When 4-chloro-2-methylhex-2-ene reacts with AgNO₃ in ethanol, two isomeric ethers are formed. Suggest structures, and propose a mechanism for their formation

Practice your electron-pushing skills by drawing a mechanism for the following S_N1 reactions.

(a)

The allylic bromide below gives two S_N1 products. Justify the formation of each.

Rank the ability of the following compounds to undergo an S_N1 reaction ( 1 = fastest, 5 = slowest ).

Propose a mechanism for each reaction, showing explicitly how the observed mixtures of products are formed.

(b) 2-methylbut-3-en-2-ol + HBr → 1-bromo-3-methylbut-2-ene + 3-bromo-3-methylbut-1-ene

When 3-bromo-1-methylcyclohexene undergoes solvolysis in hot ethanol, two products are formed. Propose a mechanism that accounts for both of these products.

Which haloalkane would you expect to undergo the fastest S_N1 reaction? Why?

Provide a mechanism for the following S_N1 reaction. What roles (acid/base/nucleophile/electrophile) does ethanol play in the reaction? What functional group is made in this reaction?

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vii) HCl; (viii) HBr; If no reaction occurs, write 'no reaction.'

(f)