Carboxylic Acids & Derivatives

RCOOH

structure of carboxylic acids

1-4 Carbons

How many carbons are quite polar

arrhenius acid

a substance that incerases H+ or H3O+ in water

Bronsted-Lowry acids

proton (H+) donor

-oic acid

iupac naming of carboxylic acids

fomic acid

old name of methanoic acid

Na formate

salt form of methanoic acid

acetic acid

old name of ethanoic acid

Na acetate

salt form ethanoic acid

propionic acid

common name of propanoic acid

Na propionate

salt form of propanoic acid

butyric acid

common name of butanoic acid

Na butyrate

salt form of butanoic acid

smelly/ rancid butter/ vomit-like

odor of butanoic acid

salt

product if carboxylic acid acidic H+ is replaced with a metal (like Na+); base + acid = ?

benzoic acid

Para-aminobenzoic acid (PABA)

traditional name of benzoic acid

benzoic acid

1. causes skin irritation

2. cheap preservative

3. convert to Na benzoate in food

pyruvic acid

final product of glycolysis

keto acid

pyruvic acid (has C=O + COOH)`

“oxo”

means extra oxygen = ketone present

‘dioic acid”

2 carboxylic acids in naming

Gamma-Aminobutanoic Acid (GABA)

butanoic acid with amino group (NH2) attached

Alpha (α), Beta (β), Gamma (γ) carbons in carboxylic acids

Greek letters are used to name carbon atoms based on their position relative to the carboxyl group (–COOH).

α-carbon

carbon directly attached to –COOH

β-carbon

second carbon from –COOH

γ-carbon

third carbon from –COOH

GABA

major inhibitory neurotransmitter in the brain

high polarity and high water solubility

polarity and water solubility in short chains

low polarity and low water solubility

polarity and water solubility in long chains (6 and above Carbons)

fatty acids

long chains are also called as?

carboxylic acids derivatives

compounds derived from carboxylic acids; the -OH part is replaced by another group

1. Acid anhydride

2. Acid halide

3. Amide

4. Ester

(A-A-A-E)

main derivatives of carboxylic acids

Nucleophilic Acyl Substitution

Main reaction of Carboxylic Acid derivatives

acid anhydride

structure: combination of 2 carboxylic acids

acid anhydride

anhydide

this means “no water”

remove water

formation of acid anhydride

hydrolysis; add water

breaking/ separation of anhydride is called? and what to do?

keep “-oic” then replace “-acid” with “-anhydride”

iupac naming of anhydride

RCOOR

structure of esters

fruity/ sweet odors

odor of esters

esterification

rxn in esters

esterification or Fische esteification

formation of ester from carboxylic acid and alcohol

metyl methanoate

methanoic acid + methanol iupac name?

acetic acid + isomyl alcohol

isomyl acetate

banana scent

scent of isomyl acetate

RCOX

structure of acid halides

acid halides

the vey reactive derivative

replace “oic acid with “oyl chloride”

iupac naming of acid halides

ethanoyl chloride

acetyl chloride

common name of ethanoyl chloride

RCONH2

structure of Amide

Carboxylic acid derivative + Ammonia or Amine

composition of amides

replace “oic acid” with “amide”

iupac naming of amide

acetamide

common name of ethanamide

lactones

other name of cyclic esters

cyclic esters

cyclic RCOOCH3

hydrolysis of esters

reverse of esterification

saponification

base hydrolysis of ester; used in soap making

carboxylate ion (soap) and glycerol (alcohol)

product of saponification process

triglycerides (lipids) and stong base/ alkali (NaOH, KOH)

reactants in saponification process

neutralization

a chemical process wherein acid and base are combined together and their properties are cancelled whic produces salt and water

esteification

acid + alcohol = esterr

hydrolysis

ester + water = acid + alcohol

poor leaving groups

attached in ketones and aldehydes

good leaving groups

found in caboxylic acid derivatives

Ibuprofen

drug; a propionic acid derivative

Ketorolac

drug; acetic acid derivative