Organic Reactions Summary Sheet

Organic Reactions Summary Sheet Reactants Alkanes + Oxygen

Products

Conditions

Complete: CO2 and water

Little bit of heat to get it going and plenty of oxygen Little bit of heat to get it going, and not enuf O2, oxygen is limiting reactant UV light, hv

Incomplete: CO and water + Halogen (F2, Cl2, Br2, I2)

haloalkane

Classification Combustion (also redox reactions)

Example

Uses /Other

2 C4H10 + 13 O2  8 CO2 +10h2o CO harmful to humans, unburned hydrocarbons produce smog

2 C4H10 + 9 O2  8 CO + 10 H2O

Substitution

H H

H H

+

H

hν

Cl Cl

Cl

H

H

hν

Cl

H

methane

H

hν

Cl

Cl

Cl

H

chloromethane

hν

Cl

dichloromethane

+ hydrogen

+ acid halide (HF, HCl, HBr, HI) + water

Addition

Dihaloalkane

Alkane

Platinum or palladium catalyst

Addition

Haloalkane

Alcohol

Addition (also called reduction)

Acid conditions

Addition

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

Alcohols + Carboxylic acid + oxidizing agent (KMnO4 or K2Cr2O7)

Ester + water

Acidic solution and heat

chloroform

For incomplete oxidation: Distillation in acidic aqueous soln

Cl Cl

H

P

+

t2 / O P

H H

d

Br2 dissolved in dichloromethane is used to distinguish between alkenes and alkanes. If reddish-brown color of Br2 disappears when added to unknown, the unknown has alkenes in it.

Hydrogenation of oil for margarine

H H H H H

+

Haloalkanes are useful starting materials for organic syntheses

H Cl

H Cl

H

H H H

+

H

O

a c i d

H

commercial manufacture of ethanol

H H H

O

Condensation

H

H

tetrachloromethane also: carbontetrachloride

Uses: makes starting material for PVC and Indication of akenes

Cl Cl H H

CH3

H3C

Primary: Aldehyde

+

Cl Cl

also: trichloromethane

Alkenes + halogen (F2, Cl2, Br2, I2)

Cl Cl

O H H CH3 O

+ H3C

OH

OH

Oxidation OH propan-1-ol

a c ∆i d

,

H3C

+

K 2C

2

Or 7

O

CH3

a c i d

O H 1-propanal

Esters are used in flavouring agents, plasticizers, as solvents in perfume, polyesters

Primary: Carboxylic Acid Secondary: ketone

For complete oxidation: Heat under reflux in acidic aqueous soln Heat under reflux in acidic aqueous soln

+

OH

K 2C

2

a c i d

Or 7

O OH propanoic acid

propan-1-ol

+

OH

K 2C

2

Or 7

a c i d

O

butan-2-ol

Carboxylic acid + alcohol

Ester, see above example Amide + water

+ amine

+ base (e.g. NaOH)

See above

Condensation

difficult to conduct since amine (a base) and acid neutralize each other. Other rxns that “protect” F.G. are required

Condensation

See above

Amide, see above example

O + H3C

H3C

OH

NH2

a c ∆i d

O NaOH a c ∆i d , OH H3C

,

H3C

Condensation

See above

Distillation Apparatus

CH3

O-Na

+ H2O

See above

See above

Heating under reflux condensing tube

water out aldehyde vapor

NH

condensing tube

water in

water in boling solution

To distill you heat up the solution and collect the vapor

peptide bond formation, polymerization reactions to make nylons

O

+

H3C

Amine + Carboxylic acid

See above

O

Neutralization

Organic salt and water

butan-2-one

water out vapor condenses and falls back into flask

condensed aldehyde out

boling solution

heat under reflux means you want to heat it for a long time w/o having it evaporate to heat under reflux you need to attached a condensing tube to your flask so that vapors condense before they can escape