A2- Acyl Chlorides
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What is the structure of acyl chlorides?
RCOCl
What is an acyl chloride an example of?
acid derivative
What reactants are used to make acyl chlorides?
COOHs and SOCl2 (sulfur dichloride oxide)
What is produced in the formation of acyl chlorides?
–> acyl chloride + SO2 + HCl (g)
Why are the products of the reaction forming acyl chlorides not pure? How can they be purified?
as one reactant has to be in excess purify by distillation
What cannot be present in the formation of acyl chlorides?
WATER
What reactions do acyl chlorides undergo?
addition-elimination
What is always produced in addition-elimination reactions of acyl chlorides?
HCl gas (H comes from OH group, Cl comes from acyl chloride)
Write the general equation for the reaction between an acyl chloride and water
acyl chloride + water –> carboxylic acid + hydrogen chloride gas
Write the general equation for the reaction between an acyl chloride and ethanol
acyl chloride + ethanol –> (ethyl X) ester + hydrogen chloride gas
Write the general equation for the reaction between an acyl chloride and concentrated NH3
acyl chloride + ammonia –> amide + hydrogen chloride gas
Write the equation for the reaction between an ethanoyl chloride and CH3NH2
ethanoyl chloride + CH3NH2 –> N-methylethanamide + HCl
What is formed when reacting an acyl chloride with a primary amine?
N-substituted amide
What is observed when acyl chlorides react?
• white misty fumes • vigorous reaction
What mechanism do acyl chlorides react by?
nucleophilic addition-elimination
Why are acid anhydrides prefered over acyl chlorides when forming esters/in reactions in industry?
• acyl chlorides produce toxic HCl gas • cheaper, less reactive, reactions more easily controlled • by products are carboxylic acids