1. Show the alcohols you would obtain by reduction of the following carbonyl compounds:

(a) CH₃                  (b)          (c)  O      CH₃
       |                                                         ||         |
     CH₃CHCH₂CHO                                  CH₃CH₂CCH₂CHCH₃

2. Give the structures of the major products you would obtain from reaction of phenol with the following reagents:

(a) Br₂ (1 mol)                                                (b) Br₂ (3 mol)
(c) NaOH, then CH₃I                                       (d) Na₂Cr₂O₇, H₃O⁺

3. How would you prepare the following compounds from 2-phenylethanol?
(a) Benzoic acid
(b) Ethylbenzene
(e) 1-Bromo-2-phenylethane
(d) Phenylacetic acid (C₆H₅CH₂CO₂H)
(e) Phenylacetaldehyde (C₆H₅CH₂CHO)

4. What products would you obtain from reaction of 1-methylcyclohexanol with the following reagents?
(a) HBr
(b) H₂SO₄
(e) CrO₃
(d) Na
(e) Product of part (d). then CH₃I

5. What products would you obtain from reaction of butan-1-ol with the following reagents?

(a) BBr₂        (b)CrO₃, H₃O⁺
(c) CrO₃        (d) A periodinane