Carbonyls/ Carboxylic acids derivatives and esters (module 6 )

General equation for carboxylic acid reactions

RCOOH ⇌ H⁺ + RCOO⁻

Acid + carbonate reaction

Carbonate+ acid → salt + CO₂ + water

What are the acid + NH₃ products

RCOONH

what type of acids are carboxylic acids

weak acids (⇌ for partial dissociates)

what are acids

proton donors

what is carbon 1 in a carboxylic acid 

carbon attached to the COOH

naming carboxylic acids ( image)

state carbon chain then add a dioic acid 

How to name 2 COOH groups ( image)

Add dioic acid

Why are carboxylic acids soluble

They can form hydrogen bonds with H₂O

Name this molecule

Benzene-1,2-dioic acid

Name of benzene with 1 COOH group

Benzoic acid

Trend of carboxylic acid solubility

Longer the carbon chain the less soluble

More of the non polar carbon skeleton

What are the first 4 carboxylic acid solubility

Dissolve completely in water ( they are misible)

name of ion formed when ethanoic acid dissociates

ethanoate ion → CH₃COO⁻

name of benzoic acid dissociation ( image)

How do carboxylic acids react

Dissociate into a carboxylate ion and H⁺

general reactions of carboxylic acids

carboxylic acid + metal→ salt + H₂

carboxylic acids + carbonate → Salt + CO₂ + H₂O

carboxylic acids + Base → salt + H₂O

what is the salt that carboxylic acids forms

carboxylate ion + metal ion

methanoic acid + mg →

2HCOOH + Mg →(HCOO⁻)₂Mg + H₂

structure of a ester ( image)

naming esters 

prefix comes from alcohol ( alkyl)

suffix comes from carboxyl acid ( ends in oate)

name this ester

what are the 3 ways to make a ester

carboxyl acid + alcohol → ester + H₂O

acid anhydride + alcohol → ester + carboxylic acid

Acyl chloride + alcohol → ester + HCl

conditions for esterification ( alcohol + carboxylic acid)

conc H₂SO₄

Heat

what happens during esterification

alcohol loses OH

carboxylic acid loses H

H₂O formed

what type of reaction is esterification

condensation reaction

esterification image

reactants of forming acid anhydrides 

carboxylic acid + carboxylic acid

what is a acid anhydride

2 carboxylic acids joined together due to elimination of H₂O

acid anhydride forming ( Image)

structural formula of acid anhydrides

( identical R group)₂O

(R₁)(R₂)O

how do acid anhydrides form

esters 

acid anhydrides + alcohol → esters + carboxylic acid 

acid anhydride + alcohol reaction explained

alcohol ( hydroxyl group) loses H

carboxylic acid formed is R group gains H

how to name acid anhydrides 

number of carbon in R group ( if 3)

propanoic anhydride 

acid anhydride forming ester image

does making esters using acid anhydrides require catalyst

doesn’t require conc H₂SO₄

products of all acyl chloride reactions

all make HCl (g))

how do acyl chlorides react

HCl is removed

disadvantages of acyl chlorides reactions

make HCl which is toxic

how to know if HCl is made in a acyl chloride reaction

misty/ white fumes is produced

products of acyl chloride + water ( hydrolysis) word equation

acyl chloride + H₂O → carboxylic acid + HCl

products of acyl chloride + water ( hydrolysis) symbol equation

R - COCL + H₂O → R- COOH + HCL

what is Acyl chloride

Derivative of carboxylic acid OH is replaced by Cl

acyl chloride structure 

products of acyl chloride + alcohol / phenol word equation

acyl chloride + alcohol → ester + HCl

products of acyl chloride + alcohol / phenol symbol equation

R - COCL + R-OH → R -COO-R + HCl

advantages of using a acyl chloride to make a ester 

Higher ester yield 

products of acyl chloride + ammonia word equation

acyl chloride + ammonia → primary amide + HCl

products of acyl chloride + ammonia symbol equation

R-COCL + NH₃ → R-CONH₂ + HCl

products of acyl chloride + amide word equation

acyl chloride + amide → secondary amide + HCl

products of acyl chloride + amide symbol equation

R - COCl + R- NH₂ → R-CO- NH-R + HCl

how to form a acyl chloride

carboxylic acid + SOCl₂

carboxylic acid + SOCl₂ products

acyl chloride + SO₂ + HCl

effect of water on making acyl chloride

acyl chloride produced reacts with carboxylic acid

no water present

what are the two type of hydrolysis of esters

acid hydrolysis

base hydrolysis

conditions for acid hydrolysis

heat under reflux

dilute H₂SO₄

products of acid hydrolysis

carboxylic acid + alcohol

Acid hydrolysis ( image)

Base hydrolysis ( image)

Conditions for base hydrolysis

heat under reflux

Dilute alkali ( NaOH)

acid hydrolysis reaction

Phenols + acyl chloride image