Carboxylic Acids and Derivatives

What is the functional group of a carboxylic acids?

COOH, carbonyl (C-O double) and OH acid

How are carboxylic acids produced?

Oxidation of primary alcohols under reflux

What happens to carboxylic acids when they are in solution?

they are weak acids so dissociate slightly, forming a H+ ion and a carboxylate ion (RCOO-)

How do carboxylic acids react with carbonates?

They react as acids to produce a carboxylate salt, water and CO2

Why are small chain carboxylic acids soluble in water?

They can form hydrogen bonds with water molecules (between the lone pair on an oxygen atom and the positive part of the hydrogen atom)

How are esters formed and what is it called?

When carboxylic acids react with alcohols in the presence of a strong acid catalyst

Esterification

What molecule is each part of the water molecule removed from in esterification?

The OH is removed from the acid and the H from the alcohol

What are esters?

Sweet smelling compounds used in food flavourings and perfumes

What are the relative boiling points of esters?

Low

Vegetable oils and fats are esters of what naturally occurring alcohol?

Glycerol (propane - 1,2,3 - triol)

What is formed when glycerol undergoes esterification?

Triglyceride esters

What is ester hydrolysis?

When a water molecule is added across an ester to split it into multiple products

What happens to an ester when it is hydrolysed in acidic conditions?

The alcohol and carboxylic acid that make up the ester are reformed

What happens when an ester is hydrolysed under basic conditions?

The alcohol is reformed and the carboxylic acid reacts further to form a carboxylate salt

What is the formation of a carboxylate salt from an ester called?

Saponification

State a common application of carboxylate salts and why.

Soap

They have both hydrophilic and hydrophobic properties

What is acylation?

The introduction of an acyl group to another molecule

What is an acyl group?

An R group bonded to a C-O double bond

State what 2 types of molecules acyl group can come from.

Acyl chlorides

Acid anhydrides

What is an acyl chloride?

A molecule with a C-O double bond directly bonded to a Cl atom

What is an acid anhydride?

State the general reaction for acylation.

Nucleophile + Acyl —> Nucleophile - C[O]R + leaving group

State the conditions for an acylation reaction. 

Room temp, no catalyst, anhydrous

What products are made during an acylation reaction using water as the nucleophile?

Carboxylic acid + HCl (hydrogen chloride)

What products are made during an acylation reaction using an alcohol as the nucleophile?

Ester + HCl

What products are made during an acylation reaction using ammonia as the nucleophile?

Amide + HCl

What products are made during an acylation reaction using a primary amine as the nucleophile?

N-substituted amide + HCl

What is the name of the mechanism for acylation?

Nucleophilic addition elimination

What is the suffix for an acyl chloride?

-oyl chloride

What is the formula for an acyl chloride? 

RCOCl

What is the suffix for a primary amine?

-ylamine

State the formula for a primary amine.

RNH₂

What is the suffix for an amide?

-amide

What is the formula for an amide?

RCONH₂

What is the suffix for an N-substituted amide?

N -yl -amide

What atom should be included in the structural formula of an N-sub amide that is not normally included?

The H on the nitrogen

Describe the mechanism of acylation with any nucleophile.

1. The lone pair on the nucleophile bond to the carbon in the acyl group and the C-O double bond breaks 

2. The double bond is reformed, the electrons in the C-Cl bond move to the Cl (or other leaving group) and the Cl leaves the molecule

3. The electrons in an N-H or O-H bond move to the O⁺/N⁺ and the H leaves the molecule

4. The final products are formed