Chapter 17 Flashcards
Amide
-NH2 , -NHR, or -NR2 bonded to a carbonyl
> No smell
> do not act as bases (don’t accept H+)
Esters
Carbonyl with a -OR bond
>colorless, volatile liquids, pleasant smells
> form 4 hydrogen bonds
Carboxylic acid + alcohol —»
Ester + water
Carboxylic acid + amine —-»
Amide + water
Carboxylic acid has..
The highest boiling point of all functional groups > can form 5 hydrogen bonds >highly polar > pka 3-6 > very water soluble > awful smells > weak acids
Boiling point order of functional groups
Highest-lowest: >Carboxylic acid >alcohols >aldehydes >alkanes (more carbons than hydrogen bonds)
Formic acid (monocarboxylic)
1C
HCOOH; in ant stings
Acetic acid (monocarboxylic)
2C
CH3COOH; vinegar
Propionic acid (monocarboxylic)
3C
CH3CH2COOH; sour taste in yogurt, preservative in bread
Butyric acid (monocarboxylic)
4C
CH3CH2CH2COOH; odor of rancid butter
Oxalic acid (dicarboxylic acid)
2C
Malonic acid (dicarboxylic acid)
3C
Succinic acid (dicarboxylic acid)
4C
Gultaric acid (dicarboxylic acid)
5C
Polyfunctional groups
> alkene: unsaturated acids
alcohol:hydroxy acids
ketone: keto acids
Amine: animo acids
Substituent groups
> alcohol: -hydroxy-
ketone/aldehyde: -oxo-
amine: -amino-
ether: -alkoxy
Carboxylic acid + Amine —»
Amide+ water
Cyclic Amide
Lactam
Benzoic acid
Preservative in soda
Citric acid
Present in citrus fruits & sodas
Carboxylate ion
Negative Ion informed from the acid
Acetic acid—> acetate ion (common name) or….
Ethanoic acid—> ethanoate ion
Carboxylic acids react with
Strong bases to produce a Carboxylic acid salt
Carboxylic acid can exist on two forms:
> Carboxylate ion in an base (high pH & water solubility)
Carboxylic acid form in an acid ( low pH & water solubility)
-form depends on pH
Saponification
Ester hydrolysis by reaction with a base such as NaOH or KOH
Product of reaction is carboxylate anion
Addition of phosphate to a biomolecule …
Adds negative charge to biomolecule
