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1

butyric acid

common name for butanoic acid

means butter

1

reactuib if a carboxylic acid with an alcohol (or phenol) to produce an ester (and water)

a strong acid catalyst is needed

opposite is hydrolysis

esterification

1

smaller ones are colorless liquids  with pleasant odors

  -responsible for flavor & fragrance of fruits & flowers

  -used as flavoring agents in foods

physical state of esters

2

esters

carboxylic acid derivative where OH is replaced with an OR group

represented linearly as -COOR

odor - fruits/flowers

2

common name for butanoic acid

means butter

butyric acid

3

carboxyl group

a carbonyl group (C double bonded to O) with a hydroxyl group bonded to the carbonyl carbon atom.

written linearly as -COOH

3

carboxylic acid derivative that looks like 2 acid molecules linked together. very reactive

"without water"

reacts with water (produces 2 acid molecules)

reacts with alcohol (produces ester and acid)

reacts with amines (produces acid and amide)

acid anhydrides

4

chemical reaction of esters

ester plus a strong base results in a carboxylate salt and an alcohol

saponification reaction

6

acetic acid

common name for ethanoic acid

means sour

7

order of reactivity

Acid chloride  >  acid anhydride  >  ester = acid  >  amide

7

a carbonyl group (C double bonded to O) with a hydroxyl group bonded to the carbonyl carbon atom.

written linearly as -COOH

carboxyl group

8

acyl compound

contains an acyl group whose carbonyl compound atom is bonded directly to an O, N or halogen

9

common name for pentanoic acid

means strong

valeric acid

10

saponification reaction

chemical reaction of esters

ester plus a strong base results in a carboxylate salt and an alcohol

11

sulfur analog of esters

a sulfur containing analog of an ester where an SR group replaces the ester's OR group

an important example is Acetyl coenzyme CoA - plays a central role in metabolic cycles where the body obtains energy to run itsefl

thioesters

11

carboxylic acid derivative where the OH part of the carboxyl group is replaced with a Cl

reactive with water (produces acid and alcohol)

reactive with alcohol (produces ester and acid)

reactive with amine (produces amide and acid)

acid chloride

11

β-keto ester

result of Claisen Condensation

has 2 O double bonds

12

boiling point higher than alcohols because they can form 2 hydrogen bond with other molecules creating a dimer

boiling point of carboxylic acids

12

skin care products

contains an –OH on the α carbon

α-hydroxy acids

13

valeric acid

common name for pentanoic acid

means strong

13

acid anhydrides

carboxylic acid derivative that looks like 2 acid molecules linked together. very reactive

"without water"

reacts with water (gives 2 acid molecules), alcohol (gives ester) and amines (gives acid and amide)

15

boiling point

  carboxylic acids > alcohols > [aldehydes, ketones, esters, ethers] > alkanes

16

contains an acyl group whose carbonyl compound atom is bonded directly to an O, N or halogen

acyl compound

17

formic acid

common name for methanoic acid

means sting

18

Claisen Condensation
 

reaction of esters

The α-carbon of esters is Acidic (like aldehydes & ketones)

the acidic H is removed by the strong base, allows the α-carbon to act as a nucleophile and attack the carbonyl carbon of a 2nd ester molecule

results in alcohol and β-ketoester

19

solubility of carboxylic acids

smaller ones are soluble because they form hydrogren bonds with water

20

reaction of esters

The α-carbon of esters is Acidic (like aldehydes & ketones)

the acidic H is removed by the strong base, allows the α-carbon to act as a nucleophile and attack the carbonyl carbon of a 2nd ester molecule

results in alcohol and β-ketoester

Claisen Condensation
 

21

acyl group

the acid part of an ester

the RCO- portion of a molecule

e.g. common names - formate, acetate

23

lactone

cyclic esters

formed when hydroxy acids (compounds with hydroxyl and carboxyl groups) undergo intermolecular esterification

24

thioesters

sulfur analog of esters

a sulfur containing analog of an ester where an SR group replaces the ester's OR group

an important example is Acetyl coenzyme CoA - plays a central role in metabolic cycles where the body obtains energy to run itsefl