PHOrgChem (Lecture) | Module 9 (PART 3: REACTIONS OF CARBOXYLIC ACID, ESTER, AMIDE, ACID ANHYDRIDE, ACID HALIDE, and THIOESTER)

Esterification, and Amide Formation

Reactions of CARBOXYLIC ACIDS

Hydrolysis, and Transesterification

Reactions of ESTERS

Hydrolysis, and Reduction

Reactions of AMIDES

Hydrolysis, Ester Formation, and Amide Formation

Reactions of ACID HALIDES

Hydrolysis, and Nucleophilic Substitution

Reactions of THIOESTERS

Esterification

When a carboxylic acid reacts with an alcohol in the presence of an acid catalyst (like H₂SO₄), it forms an ester and byproduct of water.

Sulfuric acid

When a carboxylic acid reacts with an alcohol in the presence of an acid catalyst (like __________), it forms an ester and byproduct of water.

Esterification

Carboxylic acid + alcohol → ester + water

Methyl Acetate + Water

Acetic acid + Methanol → _______ + ________

Esterification

A few drops of acid (SULFURIC ACID) helps the reaction

Esterification

Acetic acid and Methanol combine and release a water molecule, leaving behind Methyl acetate

Methanol

ESTERIFICATION: CH₃COOH + CH₃OH → CH₃COOCH₃ + H₂O

• This is a simple type of alcohol

Methyl Acetate

ESTERIFICATION: CH₃COOH + CH₃OH → CH₃COOCH₃ + H₂O

• ester; sweet fruity smell compared to initial acid (acetic acid)

Amide Formation

A carboxylic acid reacts with ammonia (or an amine) to form an amide and release water

Amide Formation

Carboxylic acid + amine → amide + water

Amide + Water

Carboxylic acid + amine → _____ + _____

Acetamide

Acetic acid and Ammonia combine and release a water molecule, leaving behind __________

Amide Formation

An acid combined with a base-like compound will form an amide and give off water

Acetic Acid

AMIDE FORMATION:
CH₃COOH + NH₃ → CH₃CONH₂ + H₂O

• acid; sour smelling

Ammonia

AMIDE FORMATION:
CH₃COOH + NH₃ → CH₃CONH₂ + H₂O

• base; sharp smelling gas used in cleaning products

Acetamide

AMIDE FORMATION:
CH₃COOH + NH₃ → CH₃CONH₂ + H₂O

• amide

Hydrolysis

“Splitting with water”

Hydrolysis

Rewind of esterification

Esterification

Hydrolysis is rewind of?

Hydrolysis

Common reaction of esters, they easily undergo ________

Acid, or Base

When esters are heated with water and an ____, or ____ (helps with the reaction), they break back into the acid and alcohol they came from.

Hydrolysis

Ester + water → carboxylic acid + alcohol (acid or base catalyzed)

Acetic acid, and Methanol

HYDROLYSIS:
CH₃COOCH₃ + H₂O → CH₃COOH + CH₃OH

• When Methyl acetate comes in contact with water, it splits into its two original form, namely?

Methyl Acetate

HYDROLYSIS:
CH₃COOCH₃ + H₂O → CH₃COOH + CH₃OH

• ester; pleasant fruity smell

Transesterification

One alcohol in the ester is swapped for another, forming a new ester.

Transesterification

Ester + alcohol → new ester + alcohol

New Ester, and Alcohol

TRANSESTERIFICATION:
CH₃COOCH₃ + C₂H₅OH → CH₃COOC₂H₅ + CH₃OH

• When ester combines with alcohol, they exchange groups = ?

Ethyl Acetate, and Methanol

TRANSESTERIFICATION:
CH₃COOCH₃ + C₂H₅OH → CH₃COOC₂H₅ + CH₃OH

• The methyl group of the ester switches place with the ethyl group of the alcohol, forming?

Ethanol

TRANSESTERIFICATION:
CH₃COOCH₃ + C₂H₅OH → CH₃COOC₂H₅ + CH₃OH

• alcohol common in alcoholic beverages

Ethyl Acetate

TRANSESTERIFICATION:
CH₃COOCH₃ + C₂H₅OH → CH₃COOC₂H₅ + CH₃OH

• ester with a fruity smell

Amide

They are more stable than esters when it comes to reaction with water

Hydrolysis

Under heat and acidic/basic conditions, amides break down into acids and amines.

Acid, and Amine

Under heat and acidic/basic conditions, amides break down into?

Hydrolysis

Amide + water → carboxylic acid + amine (acid or base catalyzed)

Acetic Acid, and Ammonia

HYDROLYSIS:

CH₃CONH₂ + H₂O → CH₃COOH + NH₃

• Water breaks the amide bonds, splitting Acetamide into?

Reduction

Amides can be reduced to amines using agents like LiAlH₄.

Lithium Aluminum Hydride

Amides can be reduced using agents like?

Reduction

Amide + reducing agent → amine

Methylene Group

REDUCTION:

CH₃CONH₂ + [H] → CH₃CH₂NH₂

• Carbonyl group of the amide is reduced by adding hydrogen atom, turning the carbonyl into a?

Ethyl Amine

REDUCTION:

CH₃CONH₂ + [H] → CH₃CH₂NH₂

• Acetamide then turns into?

Hydrogen Atom

REDUCTION:

CH₃CONH₂ + [H] → CH₃CH₂NH

• can be from reducing agent which can be hydrogen gas or a substance that donates electrons and protons

Ethyl Amine

REDUCTION:
CH₃CONH₂ + [H] → CH₃CH₂NH

• simple amine; used in various chemical processes (EX: production of pharmaceuticals)

Hydrolysis

Acid halides react violently with water to give carboxylic acids.

Carboxylic Acid

Acid halides react violently with water to give?

Hydrolysis

Acid halide + water → carboxylic acid + HX

Acetic Acid, and Hydrochloric Acid

HYDROLYSIS:

CH₃COCl + H₂O → CH₃COOH + HCl

• Water reacts with Chlorine atom(attached to carbonyl) which splits the compound into two parts, namely?

Acetyl Chloride

HYDROLYSIS:

CH₃COCl + H₂O → CH₃COOH + HCl

• reactive compound made of Acetic acid with Chlorine

Hydrochloric Acid

HYDROLYSIS:

CH₃COCl + H₂O → CH₃COOH + HCl

• strong acid found in cleaning products

Ester Formation

Acid halides react easily with alcohols to form esters.

Ester Formation

Acid halide + alcohol → ester + HX

Methyl Acetate

ESTER FORMATION:

CH₃COCl + CH₃OH → CH₃COOCH₃ + HCl

• In the reaction, Methanol gives up methyl group to combine with acetyl group of Acetyl chloride, forming?

Hydrochloric Acid

ESTER FORMATION:

CH₃COCl + CH₃OH → CH₃COOCH₃ + HCl

• Chlorine is then released as?

Amide Formation

They also react with ammonia or amines to form amides

Amide Formation

Acid halide + amine → amide + HX

Acetamide

AMIDE FORMATION:
CH₃COCl + NH₃ → CH₃CONH₂ + HCl

• In the given reactions, the chlorine atom is swapped for an amine group (NH) in ammonia, forming?

Hydrochloric Acid

AMIDE FORMATION:
CH₃COCl + NH₃ → CH₃CONH₂ + HCl

• Chloride combines with hydrogen from ammonia (byproduct), producing?

Hydrolysis

Like esters, thioesters can be hydrolyzed to yield a carboxylic acid and a thiol.

Carboxylic Acid, and Thiol

Like esters, thioesters can be hydrolyzed to yield a?

Hydrolysis

Thioester + water → carboxylic acid + thiol

Acetic Acid

HYDROLYSIS:
CH₃COSCH₃ + H₂O → CH₃COOH + CH₃SH

• Sulfur separates from acetyl group and acetyl combines with water to form?

Methyl Mercaptan

HYDROLYSIS:
CH₃COSCH₃ + H₂O → CH₃COOH + CH₃SH

• Sulfur then becomes ____________ (strong foul smell, like rotten eggs)

Nucleophilic Substitution

Thioesters are reactive in biological systems, transferring acyl groups to build molecules

Nucleophilic Substitution

Thioester + nucleophile → new compound

Acetyl-CoA

In biology, this reacts with various nucleophiles to transfer the acetyl group.

Acetyl-CoA

It is a molecular delivery truck that carries acetyl groups to various places in the cell. It is essential for various biological processes like energy production and building molecules

Acetyl Group

Acetyl-CoA encounters molecules with nucleophilic group ready to bond with?

CoA

Acetyl-CoA transfers acetyl to protein/enzyme, modifying it and changing its activity. This also regulates various biological processes like gene expression or metabolism. At the end of this reaction, the Acetyl-CoA becomes?