Carboxylic Acids

Chapter 20 guide to carboxylic acids

Acid halides > anhydride > esters > amides

What is the order of reactivity of molecules in a nucleophilic acyl substitution reaction?

Begin with acid halides > …

E.W.G.

Which is more acidic?

E.W.G. or E.D.G

(withdrawing) or (donating)

acidity of carboxylic acid

What does the R group determine?

cyclohexanecarboxylic acid

What is the common name of this structure?

1

When number in nomenclature, what number is the carbon carbonyl given?

-oic acid

In nomenclature, the parent name ends how for carboxylic acids?

weak (weak acid)

Br, Cl, F, I are examples of what types of electron-withdrawing groups?

strong (very acidic)

moderate (acidic)

weak (weak acid)

strong (very acidic)

NO₂, CN, N⁺R₃, SO₃H are examples of what types of electron-withdrawing groups?

strong (very acidic)

moderate (acidic)

weak (weak acid)

moderate (acidic)

-C=O groups are usually considered to be what type of electron withdrawing group?

strong (very acidic)

moderate (acidic)

weak (weak acid)

replace Br with COOH

Reagent:

NaCN

———>

H3O+, heat

replace Br with COOH

Reagent:

1.) Mg

———>

2.) CO₂

3.) H3O+

replace H with CH3

Reagent:

NaOH

———>

CH₃I