Alcohols and Phenols

Question 1

Elimination to form alkenes

Answer 1

(recap)

Excess con H2SO4, heat (or the other 2)

Question 2

Nucleophilic substitution to form halogenoalkanes

Answer 2

PCl5 (s)

Question 3

Redox with metal to form alkoxide (phenols too)

Answer 3

Na (s)

Question 4

Condensation to form ester (RCOOH ver.)

Answer 4

Carboxylic acid, con H2SO4 cat, heat under reflux

Question 5

Condensation to form ester (RCOCl ver.)

Answer 5

RCOCl

Question 6

Oxidation of primary alcohol (weak ver.)

Answer 6

K2Cr2O7, H2SO4, heat with immediate distillation
(forms aldehyde)
K2Cr2O7/KMnO4 in H2SO4 (aq), heat under reflux to give RCOOH

Question 7

Oxidation of primary alcohol (strong ver.)

Answer 7

KMnO4, H2SO4 (aq), heat under reflux to give RCOOH

Question 8

Oxidation of secondary alcohol to give ketone

Answer 8

KMnO4, H2SO4 (aq), heat under reflux to give ketone

Question 9

Test for alcohol with PCl5 (s)

Answer 9

White fumes of HCl (substitution)

Question 10

Test for alcohol with KMnO4 and H2SO4 (aq), heat

Answer 10

Primary and secondary: purple to colourless

Tertiary: remain purple

Question 11

Tri-iodoform test

Answer 11

Aqueous iodine in NaOH, add to alcohol with the specific necessary structure, warm with water bath
Brown iodine solution decolourised, pale yellow precipitate of tri-iodomethane (CHI3)

Question 12

Neutralisation of phenol

Answer 12

NaOH (aq), gives phenoxide

Question 13

Condensation of phenol to form ester

Answer 13

NaOH, acyl chloride