Aldehydes, Ketones and Carboxylic Acids

Formic acid

Acetic acid

Propionic acid

Butyric acid

Salicylaldehyde

Benzaldehyde

2-Hydroxybenzaldehyde

o-Tolualdehyde

One carbon and one hydrogen

Two hydrogen atoms

Two carbon atoms

One carbon and one hydroxyl group

Methyl ethanoate

Ethyl methanoate

Dimethyl ketone

Methyl acetate

2-Methylpentan-3-one

4-Methylpentan-3-one

3-Methylpentan-2-one

Ethyl isobutyl ketone

$\text{CH}_3\text{CHO}$

$\text{CH}_3\text{COCH}_3$

$\text{CH}_3\text{CH}_2\text{CH}_3$

$\text{CH}_3\text{OCH}_3$

3-Phenylprop-2-enal

1-Phenylprop-2-enal

3-Phenylpropanal

2-Phenylprop-2-enal

One $\sigma$-bond formed by $sp^2-sp^2$ overlap and one $\pi$-bond formed by $p-p$ overlap.

One $\sigma$-bond formed by $sp^3-sp^3$ overlap and one $\pi$-bond formed by $p-p$ overlap.

Two $\sigma$-bonds.

One $\sigma$-bond and two $\pi$-bonds.

2-methylbutanal

3-methylbutanal

2-ethylpropanal

Pentanal

Heptanedioic acid

Hexanedioic acid

Pimelic acid

Octanedioic acid

Aldehydes

Ketones

Carboxylic acids

Alcohols

Ethane

Ethanal

Ethene

Ethanoic acid

Propanal

Propanone

Propanoic acid

Ethanoic acid

$CH_3Cl$

$CH_3COCl$

$CO + HCl$

$CH_3CHO$

Propanal

Propanoic acid

Propanone

Ethyl methyl ether

Butan-1-ol

Butanal

Butan-2-one

Butanoic acid

$CO$ with $NaOH$ under pressure at $473\text{ K}$ followed by treatment with $H_2SO_4$

$CO_2$ with $H_2O$ under pressure

Methanol with $KMnO_4$

Formaldehyde with $NaOH$

Carbon dioxide

Ethyl chloroformate

Both Carbon dioxide and Ethyl chloroformate

Carbon monoxide

Birnbaum-Simonini reaction

Hoffmann bromamide reaction

Schmidt reaction

Curtius rearrangement

One

Two

Three

Four

Formaldehyde

Acetaldehyde

Acetone

Carbon dioxide

Propanal

Propenal

Butenal

Ethanal

Phenol

Ethanol

Ethanoic acid

Acetone

Solid

Liquid

Gas

Plasma

Inductive effect of the alkyl group

Resonance involving two equivalent structures

Steric hindrance

Hydrogen bonding with the solvent

Blue

Yellow-Orange

Green

Violet

Phenylacetic acid

Benzoic acid

Propanoic acid

Phthalic acid

Phosphorus trichloride ($PCl_3$)

Phosphoryl chloride ($POCl_3$)

Phosphorous acid ($H_3PO_3$)

Phosphoric acid ($H_3PO_4$)

Aldol condensation

Cannizzaro reaction

Perkin reaction

Claisen condensation

Acetaldehyde

Chloral ($CCl_3CHO$)

Acetone

Formaldehyde

Absorb water and shift the equilibrium to the right

Act as a base

Decrease the rate of reaction

Oxidize the aldehyde

Tetrahedral

Trigonal planar

Linear

Octahedral

Methanol

Ethanol

Propan-2-ol

Ethanal

Oxygen atom

Carbon atom

Both carbon and oxygen

Neither carbon nor oxygen

The product is always a pure enantiomer.

The nucleophile can attack from either side of the planar carbonyl group with equal probability, forming a racemic mixture.

The attack only happens from the side opposite to the methyl group.

The reaction does not create a new chiral center.

A primary alcohol

A secondary alcohol

A tertiary alcohol

An aldehyde

A hydrazone

An alkanolamine (addition product)

An imine

An azine

Acetone

Butanone

3-Pentanone

Cyclobutanone

The oxygen atom has a partial positive charge.

The carbon atom is the most electrophilic center due to the polarization of the $C=O$ bond.

The $C-Mg$ bond is purely covalent and the $R$ group is not a nucleophile.

Oxygen is too sterically hindered for the approach of the $R$ group.

Hemiketals are generally more stable than hemiacetals.

Hemiketals are easily isolated from the reaction of ketones and alcohols.

Ketones do not form hemiketals; they only form ketals.

The equilibrium for hemiketal formation from acyclic ketones and alcohols generally favors the reactants.

Carboxylic acid

$\beta$-hydroxy aldehyde

Primary alcohol

Alkane

Methanal

Ethanal

Chloral

Trimethylacetaldehyde

It requires a strong oxidizing agent

It is driven by the stability of the enolate ion

It only occurs in the presence of concentrated acids

It leads to the formation of an ester

$H_2$ molecule

$O_2$ molecule

$H_2O$ molecule

$CO_2$ molecule

Ketones are generally more acidic than aldehydes because they have more methyl groups.

Aldehydes are generally more acidic because the carbonyl carbon is more electron-deficient due to fewer $+I$ groups.

Aldehydes and ketones have identical $\alpha$-hydrogen acidity.

Acidity depends only on the number of $\alpha$-hydrogens, not the type of carbonyl.

But-2-enal

Propenal (Acrolein)

Pent-2-enal

3-hydroxypropanal

It preferentially abstracts the hydrogen from the more substituted $\alpha$-carbon.

It preferentially abstracts the hydrogen from the less substituted $\alpha$-carbon due to steric hindrance.

It does not abstract any hydrogen.

It abstracts all $\alpha$-hydrogens at the same rate.

$sp^{3}$

$sp^{2}$

$sp$

$p$-orbital is not involved

Cleavage of a $\beta$-hydroxy aldehyde into two carbonyl compounds.

Formation of an ether from an alcohol and aldehyde.

Oxidation of an aldehyde to a carboxylic acid.

Hydrogenation of an alkene.

The $\alpha$-hydrogen, because it is closer to the carbonyl.

The $\gamma$-hydrogen, because the resulting anion is more extendedly conjugated.

Both are equally acidic.

The $\alpha$-hydrogen, because of the $sp^{3}$ hybridization of the $\gamma$-carbon.

Benzaldehyde

Formaldehyde

Acetaldehyde

Propanal

Isoprene

Methyl methacrylate

Vinyl acetate

Styrene

Phenol-formaldehyde resin

Urea-formaldehyde resin

Vinyl resin

Polyester resin

Formaldehyde

Cyclamen aldehyde

Benzaldehyde

Acetaldehyde

Rubber

Petrochemical

Perfumery and Cosmetics

Explosives

Synthesis of resins

Synthesis of pharmaceuticals and fragrances

Manufacture of plastics

Preservation of biological specimens

Acetone

Butanone

Cyclohexanone

Cyclopentanone

As a refrigerant in industrial chillers

As a high-performance solvent for coatings and printing inks

As a synthetic sweetener for diabetic patients

As a stabilizer for explosive dynamite

Pharmaceutical industry for pill coating

Wood industry for plywood and particle boards

Food industry for thickening sauces

Textile industry for dyeing wool

Polyester (Dacron)

Nylon-6,6

Acrylic (Orlon)

Rayon

The electronegativity of the oxygen atoms

The presence of the alkyl group

The non-polar nature of the O-H bond

The presence of only single bonds

It decreases

It increases

It remains the same

It becomes 0

Ethoxide

Propanoate

Acetate

Propyl ion

Hydrogen is electron withdrawing

Methyl group has a $+I$ effect which destabilizes the carboxylate ion

Methyl group has a $-I$ effect

Formic acid has resonance but acetic acid does not

$-Cl$

$-NO_2$

$-C_2H_5$

$-CHO$

Three nitro groups provide massive $-I$ and $-R$ effects

The ortho-nitro groups cause steric inhibition of resonance, forcing the $COOH$ group out of the ring plane

Intramolecular hydrogen bonding between $COOH$ and $NO_2$

Both A and B

$HOOC-COOH$ (Oxalic acid)

$HOOC-CH_2-COOH$ (Malonic acid)

$HOOC-(CH_2)_2-COOH$ (Succinic acid)

$HOOC-(CH_2)_3-COOH$ (Glutaric acid)

Increased $-I$ effect from two hydroxyl groups.

Stabilization of the carboxylate anion by two intramolecular hydrogen bonds.

Steric hindrance forcing the carboxyl group out of the plane.

The $+R$ effect of the hydroxyl groups.

$p-Aminobenzoic\ acid$

$o-Aminobenzoic\ acid$

$m-Aminobenzoic\ acid$

$Benzoic\ acid$

The $-I$ effect of the hydroxyl group.

The $+R$ effect of the hydroxyl group.

Intramolecular hydrogen bonding in the neutral lactic acid molecule.

The larger size of the hydroxyl group.