7. Substitution Reactions

Predict the compound in each pair that will undergo solvolysis (in aqueous ethanol) more rapidly.

(c)

(d)

Choose the member of each pair that will react faster by the SN1 mechanism.

c. n-propyl bromide or allyl bromide

d. 1-bromo-2,2-dimethylpropane or 2-bromopropane

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃ ; (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ (vii) HCl; (viii) HBr; (ix) PCC; (x) H₂CrO₄ , H₂O (xi) HOCl, H₂O (xii) HIO₄ If no reaction occurs, write 'no reaction.'

(f)

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

(b)

Rationalize the ranking of increasing reaction rate of the benzylic halides shown.

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

(a)

Predict the compound in each pair that will undergo solvolysis (in aqueous ethanol) more rapidly.

(a) (CH₃CH₂)₂CH—Cl or (CH₃)₃C—Cl

(b)

In contrast, optically active butan-2-ol does not racemize on treatment with a solution of KOH. Explain why a reaction like that in part (a) does not occur.

Predict the product of the following reaction:

Draw the stereoisomers that are formed from the following S_N1 reactions:

a. 3-bromo-3-methylpentane and methanol

b. 3-chloro-3-methylhexane and methanol

Which of the following is a characteristic property of the $S{N}_1$ reaction mechanism?

Which statement best describes the organic product formed in a typical $S{N}_1$ reaction?

Predict the products of the following S_N2 reactions.

(c)

(d)

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)