Module 10: Carboxylic Acid Derivatives

To name esters you find the longest continuous chain attached to the _____ and add the suffix ___. This is the parent chain

carbonyl group, -oate

name this molecule

ethyl butanoate

to name amides, you find the longest continuous chain attached to the ____ and add the ending____. This is the parent chain. At the beginning of the name, you need to add an ___ to designate which atom the substituent is attached to.

carbonyl group, amide, N

Name this molecule

N-methyl propanamide

Name this molecule

acetic anhydride

name this molecule

benzoyl chloride

name this molecule. To name nitriles, count the longest continuous chain starting from the carbon attached to the nitrile. Youd do NOT drop the -e in this case

hexanenitrile

the carbonyl group will be more reactive when it is not ____.

stabilized

The more positive the carbonyl group, the more -___ it is.

reactive

rank amides, anhydrides, esters, and acyl halides from most stable to lest stable

amides > esters > anhydrides > acyl halides

rank amides, anhydrides, esters, and acyl halides from most reactive to least reactive.

acyl halides > anhydrides > esters > amides

the more stable an acyl carbon is, the ___ reactive the molecule will be.

less

the less stable an acyl carbon is, the ___ reactive the molecule will be.

more

one carboxylic acid derivative can be converted to another if the reaction leads to a more ____ carbonyl group.

stabilized

you can convert acyl chlorides into ?

anhydrides, esters, and amides

you can convert anhydrides into?

esters and amides

esters can be converted into?

amides

esters cannot be converted into ?

anhydrides or acyl halides, they are less stable than esters

anhydrides cannot be converted into?

acyl halides, they are less stable than anhydrides

amides cannot be converted into?

anhydrides, esters, or acyl halides, they are less stable than amides

draw the structure for acetic anhydride

draw the structure for Phthalic anhydride

draw the structure for Maleic anhydride

draw the structure for maleic acid

cyclic anhydrides are the only way to close __ or __ member rings

5 or 6

for the hydrolysis of esters in acidic conditions, each step in the mechanism is ____.

reversible

for the hydrolysis of esters in basic conditions, all steps are irreversible exceot for ___.

the last step

ester reactions with amines to get amides do not work with ____ amines.

tertiary

increasing the alkyl chain on the oxygen of an ester ____ the reactivity of that side of the molecule

decreases.

you can react esters with __, ___, and ___ to get amides.

ammonia, primary amines, and secondary amines

Lactams are _____.

cyclic amides

cyclic amides are called?

lactams

amides are not very ____.

reactive