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Organic Reactions Summary Sheet

Reactants Alkanes + Oxygen Products Complete: CO2 and water Incomplete: CO and water + Halogen (F2, Cl2, Br2, I2) Alkenes + halogen (F2, Cl2, Br2, I2) haloalkane Conditions 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
Classification Combustion (also redox reactions)

Example 2 C4H10 + 13 O2 8 CO2 +10h2o 2 C4H10 + 9 O2 8 CO + 10 H2O

Uses /Other

CO harmful to humans, unburned hydrocarbons produce smog

Substitution

H H H
methane

Cl Cl

H H H
chloromethane

Cl

H Cl H Cl

H Cl Cl
chloroform

Cl

Cl Cl Cl
tetrachloromethane also: carbontetrachloride

Cl

dichloromethane

also: trichloromethane

Dihaloalkane

Addition

H H

H H

Cl Cl

Cl Cl H H H H

Uses: makes starting material for PVC and Indication of akenes


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.

+ hydrogen

Alkane

Platinum or palladium catalyst

Addition (also called reduction)

H H

H H

H H

t2 / O P

d H

H H H H H

Hydrogenation of oil for margarine

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

Haloalkane

Addition

H H

H H
H CH3
O

+
+

H Cl

H Cl H H H
a c i d H H H O H H CH3
O

Haloalkanes are useful starting materials for organic syntheses commercial manufacture of ethanol

Alcohol

Acid conditions

Addition

H H

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

Ester + water

Acidic solution and heat For incomplete oxidation: Distillation in acidic aqueous soln

Condensation

H3C

OH
OH

+ H3C

OH

a c d i

H3C

CH3
O

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

Primary: Aldehyde

Oxidation
propan-1-ol

K 2C

Or 7

a c i d
H 1-propanal

Primary: Carboxylic Acid Secondary: ketone

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

OH propan-1-ol

K 2C

Or 7

a c i d

O OH propanoic acid

OH

K 2C

Or 7

a c i d

butan-2-ol

butan-2-one

Carboxylic acid + alcohol + amine

Ester, see above example Amide + water

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

Condensation Condensation

See above
O H3C OH
+ H3C

See above
O NH2
a c d i ,

H3C

NH

CH3

peptide bond formation, polymerization reactions to make nylons

+ base (e.g. NaOH) Amine + Carboxylic acid

Organic salt and water

Neutralization

O H3C i NaOH a c d , OH H3C


+

O O-Na
+ H2O

Amide, see above example

See above

Condensation

See above

See above

Distillation Apparatus
water out aldehyde vapor condensing tube

Heating under reflux


condensing tube water out vapor condenses and falls back into flask

water in
condensed aldehyde out

water in boling solution

boling solution

To distill you heat up the solution and collect the vapor

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

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