& Alkene

Cracking

Amines C-NH2

Alkanes
Polymer
Addition Heat under Pressure, H2, & with Ni catalyst

C-C
Free radical substitution with halogen and UV, room Temp & P heated H3PO4 acid Heat under pressure with NH3 in alcohol
Triiodomethane

2 Initiation RO Propagation termination

Reduction with LiAlH4

Alkenes C=C
Hydration/electrophylic addition

Elimination Reflux with conc alcoholic alkali, OH nd Attacks H on 2 C at lower temp

1

catalyst & High Pressure

Electrophylic addition with HX(aq) at room Temp & pressure. With X2 for dihalo If H2O present = alcohol + halo

Haloalkanes C-X Reactivity of -I > Br > Cl

Nucleophilic Substitution Heat with dilute alkali solution (H2O) Test for OH SN2 Pri I2 & NaOH(aq) for SN1 Ter ethanol only and 3 2nd alcohols = CHI3 yellow ppt

Carbon Atom Increases by 1

Nucleophilic Substitution Reflux KCN in alcohol

Nitriles R-CN
Nucleophilic Addition NaCN, base catalyst (H2O)

Nucleophilic Addition NaCN, base catalyst (H2O)

p284 Maple

All CH3CO(methy ketones) react with NaOH & I2(aq) forming CHI3 yellow ppt test
IO strong oxidizing agent

Distil from mix of alcohol & conc H2SO4 & KBr or H3PO4 & KI for iodo or PCl5 or SOCl2 for chloro

Secondary OH Distil with acidified K2Cr2O7 Warm with LiAlH4 producing secondary OH

Test with 2,4-DNPH

Ketones O c

Test reaction with AgNO3

Alkali, Cu2+

Pass alkene and o steam (300 C) over heated H3PO4 acid catalyst & SiO2 High Pressure

Dehydration/ Elimination Hot Pumice & Al2O3 or conc H2SO4 Alkaline KMnO4 cold

Alcohols
2

Primary OH Distil with acidified K2Cr2O7

p285 Maple Melting Point

Test with 2,4-DNPH

Aldehyde O C 6 H

p288 Maple

Red brown Alkali, Cu2+Fehlings ppt Cu2O [Ag(NH3)2]+Tollens Silver mirror

Aldehydes ease of oxidation

+R

H +

Warm with NaBH4 (H source) in H2O or ethanol

Warm with NaBH4 in H2O or ethanol

Reflux with excess acidified K2Cr2O7

Bases attack H atom Nucleophiles attack Alkyl O: attacks other, say H+

Nucleophile Claddition then elimination = sub

Key Oxidation Reduction

Diol (If hot acidified then further oxidised to two carboxylic acids unless C=C at end of chain then CO2 one of the products.

Alcohol reacts as a nucleophile

Carboxylic O acid C . 4 OH Acyl O Chloride C Cl . OH

HydrolysisReflux with HCl(aq) or H2SO4 or 7 Alkali

Heat with alcohol & acid catalyst

add[O] or remove [H] remove [O] or add [H]

Na

R-O-Na+ + H2

RO good nucleophile Better than OH- as R group pushes electrons away

Cl better leaving Group than OH of carboxylic acid

Ester O R-C O-R

1) Markovnikovs rule: When hydrogen halides add to asymmetrical alkenes the hydrogen goes on the carbon atom which already bears more hydrogen. + + Why? CH3CHCH3 + Br and NOT CH3CH2CH2 + Br Reason: Alkyl groups push electrons away from themselves stabilising carbocation. 2) Ziegler-Natta catalyst prevents side chain growth 3) SN2 is second order with respect to the rate of reaction. Rate is dependent on the alcohol and the alkali concentration. This is a 1 step reaction involving both reacting simultaneously. It takes place faster than the two step reaction where the slow step involves the breaking of the CO bond.

4) Two factors influence the ionisation of an acid. Firstly, the strength of the bond being broken. Secondly, the stability of the ions being formed. Consider the following explanation as to why the H+ is acidic.

Greater polarization of bond (1) leads to less polarization of bond (2) which leads to greater polarization of bond (3). H+ therefore better leaving group 1 2 3

Methanoic acid, is stronger than ethanoic acid because its ion is more stable as it does not have an alkyl group pushing electrons into the already negative end.
Diagram available at http://www.auburn.edu/~deruija/pda1_acids1.pdf accessed on 01/06

5) The reverse reaction where an ester is converted back into the alcohol and carboxylic acid is known as a hydrolysis reaction. The H+ catalyses the reaction by picking up the single-bonded oxygen of the ester forming a dative covalent bond. Under alkali conditions hydrolysis of an ester occurs without establishing an equilibrium. The OHreacts as a nucleophile.

6) The following is extracted and modified from http://www.chemguide.co.uk/organicprops/carbonyls/addelim.html accessed on 01/06/2011 Hydrazine is:

In phenylhydrazine, one of the hydrogens is replaced by a phenyl group, C6H5. This is based on a benzene ring.

2,4-dinitrophenylhydrazine, there are two nitro groups, NO 2, attached to the phenyl group in the 2- and 4- positions. The corner with the nitrogen attached is counted as the number 1 position, and you just number clockwise around the ring.

The overall reaction is given by the equation: By measuring the boiling point of the yellow solid produced the identity of the ketone or reacting aldehyde is easy to establish 7)