Substitution reactions (plain substitution, condensation, hydrolysis, esterification)

1. Alcohols, by Lucas reagent (3 and 2) to form a chloroalkane by or PCl5/PCl3/

SOCl2.
H3C

CH CH3

concHCl
/ ZnCl
2

OH

Lucas reagent

CH3CH2CH2OH + PCl5

2. Haloalkanes, using aqueous KOH and alcoholic/concentrated NH3/amine

Br
CH3

CH3

+KOH (aq)

CH3CH2Cl + NH3 (conc)

CH3CH2Cl + CH3NH2 (conc)

3. Acyl chlorides can react by substitution of the Cl to form

Carboxylic acids, RCOOH
esters, RCO2R
amides, RCONH2
a) CH3COCl + H2O

b) CH3COCl + CH3OH

c) CH3COCl + 2NH3

+Br

4. Carboxylic acids can react by substitution of the OH to form

acid chlorides, RCOCl (SOCl2, PCl5, PCl3)
esters, RCO2R (alcohols)
amides, RCONH2 (amine/ammonia)
a)

O
H3C

PCl 5

C
OH

b)

O
H3C

cH+

C
OH

c)

CH3OH

heat

Using ammonia AND HEAT (2 step reaction)

heat

CH3CH2CO2H + NH3

CH3CH2CO2H + NH3

d) Using amines to form Nsubstituted amides

heat

CH3CH2COOH + 2CH3NH2

CH3CH2COOH + 2CH3NH2