organic scheme

ammonium salt → amide

dehydration heat strongly to liberate the water

carboxylic acid → ammonium salt

neutralisation ammonia NH3, ammonium carbonate (NH4)2CO2

carboxylic acid → acyl/ acid chloride

nucleophilic substitution

SOCl2 / PCl3 / PCl5

acid/ acyl chloride → N-substituted amide

Nucleophilic addition-elimination

Ammonia/ Amine dropwise

RTP

acyl/ acid chloride → carboxylic acid

Nucleophilic addition- elimination

H2O dropwise

RTP

acid / acyl chloride → ester

nucleophilic addition- elimination

alcohol dropwise

RTP

nitrile → carboxylic acid

nucleophilic addition (hydrolysis)

H+ catalyst & water

Reflux

nitrile → 1° amine

reduction

LiAlH4 in dry ether solvent

haloalkane → nitrile

nucleophilic substitution

potassium cyanide dissolved in ethanol (KCN)

warm

carboxylic acid → ester

esterification

H2SO4 / HCl catalyst & alcohol

reflux

ester → carboxylic acid

hydrolysis

H2SO4

benzene → chlorobenzene (can be any halogen)

and catalyst regeneration

Halogenation reaction:

Cl2 and anhydrous AlCl3 RTP

Catalyst: AlCl3 + Cl2 → AlCl4^- + Cl^+

regeneration : AlCl4^- +H^+ → AlCl3 + HCl

benzene→ nitrobenzene

Nitration

55°C, Reflux , cH2SO4 + cHNO3 generates NO2+ ion

Generation: cH2SO4 + cHNO3 → HSO4^- + NO2^+ + H2O

benzene → methyl benzene

Crafts Alkylation

FeCl3/ AlCl3 catalyst + RX

Catalyst: R-Cl + FeCl3 → R^+ + FeCl4^-

Regeneration: FeCl4^- + H^+ → FeCl3 + HCl

Do the alcohol and phenol flash cards

nitrile/ amide → Carboxylic acid

acid hydrolysis :

dH2SO4 & water under reflux - goes directly

Alkaline hydrolysis: dNaOH forms carboxylate salt which then add acid to protonate and make carboxylic acid

(nitrile needs water)

carboxylic acid → amide

2 step process:

add ammonia/ ammonium carbonate to make ammonium and carboxylate salt

heat strongly to dehydrate the salt and make amide

amide → nitrile

dehydration:

agent: phosphorus (V) oxide P4O10 & heat

forms water

haloalkane → nitrile

Nuc Sub

KCN (or NaCN) dissolved in ethanol

EXTENDS CARBON CHAIN

nitrile → amine

reduction

LiAlH4 in dry ether solvent

amide → carboxylate salt

alkaline hydrolysis

dilute H2SO4

carboxylate salt → carboxylic acid

neutralisation cH2SO4

carboxylic acid → carboxylate salt

neutralisation

add NaOH

2° alcohol → ketone

oxidation APD reflux orange → green

ketone → 2° alcohol

reduction LiAlH4/ NaBH4 RTP

ester → 1° alcohol

reduction LiAlH4 or NaBH4

ketone → hydroxynitrile

nucleophilic addition, HCN (hydrogen cyanide) RTP

CA → 1° alcohol

reduction LiALH4 in dry ether solvent RTP produces also water

1° alcohol → CA

APD full oxidation orange → green reflux

1° amine → 1° alcohol

electrophilic substitution

sodium nitrate NaNO2

cold nitrous acid HNO2 in situ

5°

haloalkane → 1° amine

nuc sub

excess alcoholic ammonia

reflux

haloalkane → nitrile

nuc sub

KCN

HCN dissolved in ethanol

Warm

haloalkane → 1° alcohol

nuc sub

NaOH reflux/ warm

1° alcohol → haloalkane

HX cH2SO4

haloalkane → alkane

elimination

NaOH distilled in ethanol

reflux

alkane → haloalkane

free radical sub

UV light

Cl2 (g)

alkene → haloalkane

electrophilic addition

alkane → alkene

Cracking

alkene → 1° alcohol

hydration/ addition

cH2SO4

300°C

60-70atm

1° alcohol → alkene

elimination / condensation

cH2SO4

170°C

aldehyde → 1° alcohol

reduction

NaBH4/ LiAlH4

RTP

1° alcohol → aldehyde

partial oxidation

APD

heat

distillation

orange → green

methyl benzene → salt

oxidation

alkaline potassium manganate

reflux

salt → benzoic acid

add dilute acid to protonate salt