Saponification + Organic Rxn

Saponification

Creation of soaps, soaps emulsify lipids, have both hydrophobic and hydrophilic ends

Rxn: Ester hydrolysis

Breaking down a fat using a strong base, produces glycerol and a fatty acid salt (soap)

Reaction

Fat/Oil(triglyceride) + strong base→Glycerol + soap (metallic salts of fatty acids)

Soaps

Metallic salts of fatty acids, metal portion is hydrophilic, hydrocarbon chain is hydrophobic

Salts have positive ion and negative ion, Na end is positive and hydrocarbon side is negative

Biofuel

Triglycerides: contain a lot of energy, cannot be used in engines

Oil/fat can be converted into biodiesel which can be used in engines

Transesterification:

The fat will be turned into a biofuel, biofuel is less viscous than triglycerides

Rxn

Triglyceride + Alcohol → glycerol + ester

Use catalyst on industrial scale, like a strong base or a strong acid, strong base more commonly used as it is typically faster

Triglyceride + Methanol → glycerol + methyl ester

Organic Rxns for Alkenes

Alkene Addition Rxn

Alkene = contains double bond

Hydrogenation: requires catalyst

Adds hydrogen gas

Propene + H2 → Propane

Halogenation: no catalyst

Ethene + Br2 → 1-2 dibromoethane, halogenalkane

Hydrohalogenation

Adds hydrogen halide

No catalyst

Ethene + HBr → bromoethane

Hydration

Requires catalyst

Turns into alcohol

Ethane + H2O → ethanol

Organic Rxns for Alkanes

Elimination: going from single bond to double bonds

Dehydrogenation of Alkanes:

Removing hydrogens from an alkane, requires heat and a catalyst

Propane → Propene + H2

Dehydrohalogenation

Removing H-X from halogenoalkane

Uses concentrated strong base and heat

2bromobutane + KOH → but2ene + KBr + H2O

Dehydration of alcohols

Removing H2O from an alcohol

Uses strong acid catalyst and heat

2butanol + acid → but2ene + h2O

Organic Rxns: substitution

Single bonds are maintained, exchanging elements/groups

Halogenation of Alkanes:

Alkane reacts with halogen (X2)

One or more H is replaced with X

Requires light (UV) or heat

CH4 + Cl2 → CH3Cl + HCl

CH3 + Cl2 → CH2Cl2 + HCl

CH2 + Cl2 → CHCl3 + HCl

CH + Cl2 →CCl4 + HCl

Halogenation of Alcohols

Alcohol reacts with halogenic compound (RX)

OH is replaced with X

Pentanol + HCl → chloropentane + water

Hydrolysis of Halogenoalkanes

Reacts with water or aqueous base

X is replaced with OH

2bromobutane + H2O → 2butanol + HBr

Organic Rxns Carboxylic Acid Derivatives

Replacing OH group in carboxylic acid gets you a carboxylic acid derivative

Acid/Acyl Halides

Replacing OH with halogens, e.g. COCl, Acid Chloride

R-COOH + Halogenating agent → R-COX + byproduct

Acid Halide + H2O→ carboxylic acid + HX

Acid Anhydrides

2 Carboxylic acids added together ‘without’ water

Add two CA’s together, lose 2 H and 1 O from the OH groups, produce acid anhydride + H2O

Amides

Form from carboxylic acids and amines

Ethanoic acid + methanymine → amide + H2O

Esters

Fisher esterification

Organic Rxns Esters

Fischer Esterification

Condensation rxn

Carboxylic acid and alcohol react in the presence of an acid

Ethanoic acid + ethanol →← ester + H2O

Ethylethanoate

Propylethanoate

Amines

One or more hydrogen atoms in ammonia replaced by alkyl or aryl groups

Functional group

N-R’R’’

IUPAC name: parent alkane + amine

Primary Amines

N is bound to C and 2 H

NH2

Methanamine

Ethanamine

2propanamine

Secondary Amines

N bound to 2 C and one H

NHR’

N-methylmethanamine

N-ethylethanamine

N-methyl1propanamine

Tiertary Amines

N bound to 3C

NR’R’’

N,N-Dimethylcyclohexanamine

N,N-Dimethyl3octanamine

Aliphatic: nitrogen bound to alkyl group

Aromatic: nitrogen bound to aryl group

Amines are basic, they will accept a proton, then we can form an aminimum salt

Basicity Ranking:

Aliphatic

Ammonia

Aromatic

Amides

Form from carboxylic acids and amines**

Functional group: CONR2

IUPAC: carboxylic acids added prefix + amide

Primary Amides:

Both N attached R groups are hydrogens

Functional group: CONH2

Formation: Carboxylic acid + ammonia

Ethanoic acid + NH3 → ethanamide + water

Secondary Amides:

Only one N attached to R group is H

CONHR

Carboxyic acid + primary amine

Ethanoic acid + methanamine → N-methylethanamide

N-ethylethanamide

N-methylpropanamide

Tertiary Amides:

No N attached R group is H

CONR’R’’

Carboxylic Acid + Secondary amine

N-N-Dimmethylmethanamide

N-ethyl,N-methylbenzenamide

Lactams:

Cyclic Amides

Hydrolysis of Amides:

Adding water to split the amide

Methanamide + H2O → ethanoic acid + ammonia

Hydrolysis of Secondary Amides:

Produces carboxylic acid + primary amine

N-methylethanamide + H2O → ethanoic acid + methanamine

Hydrolysis of tertiary amide

Produces carboxylic acid + secondary amine

N-Ndimethylethanamide + H2O → methanoic acid + N-methyl