3.9 carboxylic acids part 2 Flashcards
what Is acylation
the process by which the acyl group is introduced to another molecule
what is the acyl group
-COR
what are compounds which have the acyl group as part of their structure called
acid derivatives
general formula acyl chlorides
CnH2n-1O
two important acid derivatives
acyl chlorides
acid anhydrides
which bond of the acid derivative is planar
carbonyl bond- C=O
are carboxylic acids or acid derivatives more reactive
acid derivatives- they react with nucleophiles
nucleophile
electron pair donor
nucleophiles that react with acid derivatives
H2O, ROH, NH3 and R-NH2
what are acyl chlorides hydrolysed in water to form
carboxylic acids
reagent for reaction of acyl chloride with water
water and acyl chloride
general equation acyl chloride + water
RCOCl + H2O > RCOOH + HCl (white fumes)
name of mechanism for all acylation reactions
nucleophilic addition-elimination
what do acyl chlorides react with ammonia to form
amides
reagent for acylation with ammonia
NH3 (excess)
general equation acylation with ammonia
RCOCl + NH3 > RCONH2 + HCl
what do acyl chlorides react with alcohols to form
esters
reagent acylation with alcohol
R1OH RCOCl
general equation acylation with alcohol
RCOCl+ R1OH > RCOOR1 + HCl
what do acyl chlorides react with primary amines to form
amides
reagent acylation with primary amines
R-NH2 (excess)
general equation acylation with primary amines
RCOCl + R1-NH2 > RCONHR1 + HCl
what is an N substituted amide
one of the hydrogens on the nitrogen has been substituted for a methyl group (acylation)
what do acid anhydrides undergo similar reactions to
acyl chlorides
what are acid anhydrides hydrolysed in water to form
carboxylic acids
general equation acid anhydride + water
RCOOCOR + H2O > RCOOH + RCOOH
acid anhydride + water produces
2 carboxylic acids
what do acid anhydrides react with ammonia to form
amides
general equation acid anhydrides + ammonia
RCOOCOR +NH3 > RCONH2 + RCOOH
acid anhydride and ammonia produces
amide and carboxylic acid
what do acid anhydrides react with alcohols to form
esters
general equation acid anhydride + alcohol
RCOOCOR + R1OH > RCOOR1 + RCOOH
acid anhydride and alcohol produces
ester and carboxylic acid
what do acid anhydrides react with primary amines to form
amides
general equation primary amines + acid anhydride
RCOOCOR + R1NH2 > RCONR1H + RCOOH