Organic

C:H about 1:1

at least 6 C atoms

Benzene ring

Rotate plane of polarised light, Optical Isomer

Chiral carbon

No plane of symmetry

cis-trans isomer

C=C

at least 2 diff grps attached to each C

React with hot acid (H2SO4)

to form 2 organic products

Contains ester or amide

react with HNO3 via ES

phenol

react w hot acid

oxygen gone

OH → C=C

React with acid to form a salt (rtp)

Neutralisation

Amine of Amino acid

soluble in acid

basic group

acidified with dilute acid

COO-, CN,

forms COOH

reacts with NaOH in ethanol

contains RX

product becomes C=C

reacts with hot NaOH

RX

product becomes alc

reacts with hot NaOH to form 2 organic products

ester or amide

COOH > PHENOL > OH

reactions w Na, NaOH, Na2Co3

React with NaOH, I2, warm

OXIDATION

2• alc (1R grp, 1CH3)

ketone containing CH3

COOH oxidised⁉

HCOOH OR (COOH)2

form CO2

reacted w 2,4-dinitrophenylhydrazine

carbonyl

react with PCL5, PBr3, PI3

OH or COOH

hydrolysis of amide vs ester

amide→basic (acidic forms nh4)

ester→acidic (basic forms coo-)

react w tollens, forming silver mirror

aldehyde

react w fehlings, forming reddish-brown ppt

aliphatic aldehyde

decolourises hot, acidified KMnO4

C=C, 1/2• alc grp, aldehyde

decolourises cold, alkaline KMnO4

C=C

decolourises X2 in UV light

FRS

decolourises X2 in CCl4

C=C

decolourises X2 with FeX3

benzene ring

react with alcoholic NH3

RX or amine

react with H2O to form an acid and white fumes

acyl Cl

undergo reduction w LiAlH4 in dry ether

COOH, aldehyde, ketone, CN

only 1,2 and 1,4 phenol can oxidise

become this

COOH + PCL5

BECOME ACYL CL

nitrogen cmpnd + Sn + HCL

REDUCTION

NO2 → NH2

benzene can react w X2 alone

got ED grp attached

long chain R on benzene + hot acidified KMnO4

R grp becomes COOH

long chain R grp (OH at tip) on benzene

+ acidfied hot K2Cr2O7

only the tip become COOH

R-X to R-CN

KCN in ethanol, heat

R-CN to R-COOH/R-COO- + NH3/NH4+

Acidic Hydrolysis (H2SO4), heat

OR

Basic Hydrolysis (NaOH), heat

RCN to RCH2NH2

Reduction

LiAlH4 in dry ether

R-X to R-OH

NaOH, heat under reflux

RX to C=C

NaOH in ethanol, heat

How to test for carbonyl (C=O)

2,4-dinitrophenylhydrazine, warm

forms orange ppt

add CN to carbonyl

Nucleophilic Addition

HCN, in presence of NaCN

Test for CH3 on ketone or 2• alc

I2, NaOH, warm

forms yellow ppt CHI3

Replace CH3 with O- Na+

Fehling

Test for aliphatic aldehyde

Reddish-brown ppt formed

Tollen

Test for any aldehyde

Silver mirror formed

Reduction of OH

Na rtp

OH bcm O- Na+

Esterification

COOH → H2SO4 catalyst, heat

Acyl Cl → rtp

1• alc oxidation

OH → K2Cr2O7, H2SO4, heat with immediate distillation → Aldehyde (1R grp)

OH → KMnO4, H2SO4, heat under reflux → COOH

2• alc

OH → any OA → ketone

OH to C=C

Elimination

Excess conc H2SO4, heat under reflux

Major product of OH to C=C

Most R grps

C=C is e- rich, more ED grps → better resonance → more stable

OH → Cl

PCl5, heat

OH to Br

PBr3, heat

OH to I

PI3, heat under reflux

Benzene → 1NO2

conc HNO3, conc H2SO4

if got R grp (ED) → rtp (eg Phenol)

Phenol → 3NO2

conc HNO3 at rtp

Benzene to 1X

X2 + AlX3

Phenol → 3Br

Br2

Benzene to 1R grp

RX + AlX3

Electrophilic Substituition

1. Generate Electrophile

2. Electrophilic attack of Benzene Ring

3. Form carbocation intermediate (X thing)

4. Loss of H

Methyl Benzene (any alkane/alkene attached)

OXIDATION

Form COOH on Benzene

+ H2O + xCO2(for long chain of alkane/alkene)

Reactions of Methyl Benzene

Alkane undergo what

FRS

X2, UV light

Ratio of Halogenoalkane formed

C=C mild oxidation become C-C

KMnO4, NaOH/H2SO4, cold

add 1OH to each C

Strong Oxidation C=C → C=O

Oxidative Cleavage

KMnO4, NaOH/H2SO4, heat

H attached to C become OH

H2C=O become CO2/CO3²- + H2O

Alkene → Alkane

H2, Ni

C=C → 2X

X2 in CCl4, in the dark

X added to each C

C=C → OH

steam(H2O(g)), conc H2SO4

OH on one C, H on other C

C=C → 1X

HX

X added to 1 C, H added to other C

Form highest degree carbocation

Higher degree → Most R grps (ED)

MEANS Higher dispersion of +ve charge

MEANS More stable

Test for Alkenes

Br2 in CCl4

Strong/Cold Oxidation

Test Phenol

neutral FeCl3

Br2

Distinguish Between RX

add AgNO3

fastest{ AgI, AgBr, AgCl }slowest

explain using (orbital overlap)

Added 1C to RX

KCN in ethanol

Added 1C to a carbonyl

HCN in KCN

CN to COOH

dilute H2SO4 heat

CN to amine

LiAlH4 in dry ether to CN

increase >1C

CONDENSATION

Acyl Cl + Phenol

Phenolic Ester

COOH + OH

ester

acyl Cl + amine

amide

Decrease in C

Strong Oxidation of C=C

Special Case

Oxidative Cleavage

RBr to RCl

Become Alc first

RBr + NaOH → ROH

ROH + PCl5 → RCl

RX to RNH2

NH3 in ethanol

Change in position of X

R-X to C=C first

NaOH in ethanol

Acyl Cl + H2, Pd, BaSO4

Aldehyde

Partial Reduction

Acyl Cl → Aldehyde

H2, Pd, BaSO4

Acyl Cl → 1• Alc

LiAlH4 in dry ether

What is H2, Pd/Pt/Ni

Reducing Agent

OH → C=C

conc H2SO4, heat

Alkene → COOH

Strong Oxidation

OH is ED or EW

ED

NH2 is ED or EW

ED

R grp is ED or EW

ED

COOH is ED or EW

EW

carbonyl ED or EW

EW

NO2 ED or EW

EW

C=C to Br&OH

Br2 and H2O

EA and ES reaction mechanism have

slow step

no fast step