REACTIONS OF ORGANIC COMPOUNDS

MAIN TYPES OF REACTIONS in Organic Chem (not reactions to your last test!)
She called it a Blood Bath! Look! I think shes using it to blow her nose I wonder why she wrote it in Japanese Whew! That was easy!

1) 2) 3) 4) 5) 6) 7)

Addition Substitution Elimination Oxidation Reduction Condensation Hydrolysis

Types of Substitution Reactions

Atoms added to a double or triple bond Alkene or Alkyne undergoes addition reaction to break a double or triple bond Example:

1) ADDITION REACTION

Reactant XY added to alkene makes alkane To recognize: Two reactants make 1 product

1) ADDITION REACTIONS
Common atoms that can be added to an alkene or alkyne H and OH (from H2O ) H and X (from H-X) where X= Cl , Br, or I X and X from (X2) where X= Cl , Br, or I H and H (from H2)

EXAMPLES: Addition Reactions

1)

2)

ADDITION REACTIONS: ALKENES Symmetrical molecule reacts with asymmetrical molecule to give one product.

Symmetrical

Asymmetrical

 Two asymmetrical molecules react to give two products.

Example:

RULES FOR ADDITION

+ Asymmetrical

or

Asymmetrical

Which product is favoured ?

MARKOVNIKOVS Rule
"the rich get richer" The carbon atom with the largest number of carbon atoms gets the X (halogen) or OH bind to it Therefore 2- bromobutane is favoured

2-bromobutane

Major product

1-bromobutane

Minor Product

ADDITION REACTIONS: ALKYNES

Also follow Markovnikovs rule when asymmetrical

Asymmetrical

1,1,2,2-tetrabromopropane

ADDITION REACTIONS: ALKYNES

May occur as two addition reactions:
+

2) SUBSTITUTION REACTION
A hydrogen atom or functional group is replaced by a different functional group To recognize: two compounds react to form two products.

2-bromobutane

2-butanamine

2) SUBSTITUTION REACTION
1) CH3CH2-OH + HI ethanol 2) CH3CH2-I + H2O iodoethane

3)

SUBSTITUTION REACTION Aromatics

Aromatics can only undergo substitution reactions

SUBSTITUTION REACTION Alcohols

Halogens in HCl, HBr or HI can substitute the OH group of alcohol or the reverse. For Ex: CH3-CH2-OH + HCl CH3-CH2Cl + H2O The reverse reaction: CH3-CH2Cl + OHCH3-CH2-OH + Cl(from water)

3) ELIMINATION REACTION
atoms are removed form a molecule to form double bonds. Reverse of addition To recognize: One reactant breaks into two products

ELIMINATION REACTION: Alcohol

undergo elimination when heated in presence of strong acids, for example: H2SO4 Example:

ELIMINATION REACTION: Alkyl Halides

Undergo elimination to produce alkenes

Bromoethane

ethene

hydrobromic acid

4) OXIDATION & 5) REDUCTION REACTIONS

Change in the number of H or O atoms bonded to C Always occur together One reactant is oxidized while the other is reduced For now, lets focus on reactant only

4) OXIDATION
Carbon atom forces more bonds to Oxygen or less to Hydrogen For example: formation of C=O bond Occurs in presence of oxidizing agents [O] such as KMnO4, K2Cr2O7, and O3 For now, focus on organic reactant only

 Alcohol oxidation can form an aldehyde or ketone Primary Alcohol

4) OXIDATION: Alcohol

Secondary Alcohol

Tertiary Alcohols do not oxidize

4) OXIDATION: Aldehyde
Aldehydes undergo oxidation to produce carboxylic acid Example:

5) REDUCTION REACTION
Carbon atom forms fewer bonds to Oxygen or more bonds to Hydrogen Aldehydes, ketones and carboxyliic acids can be reduced to alcohols Alkenes and alkynes can be reduced to become alkanes Occurs in the presence of reducing agents such as LiAlH4, and H2 where Hydrogen [H] is added

5) REDUCTION: Alkene

5) REDUCTION: Aldehyde/Ketone

6) CONDENSATION
two molecules combine to form a single, bigger molecule. Water is usually produced in this reaction A carboxylic acid and alcohol can condense to form an ester called esterification A carboxylic acid and amine can condense to form an amide

water adds to a bond splitting it into two Reverse of a condensation reaction Water can add to an ester or amide bond Ester + water makes a carboxylic acid and alcohol Amide + water makes a carboxylic acid and amine

7) HYDROLYSIS

1-propanol

POLYMERS
very long molecules made by linking small molecules called monomers Example: -PET(Polyethylene terephthalate ) polymers

- Plastics are polymers that can be heated and moulded into specific shapes and forms -Polyethene is made from monomer of

POLYMERS
can be synthetic or natural Synthetic polymers
man made polymer like plastics and polyester

Natural polymers
found in nature like glucose and silk

ADDITION Polymerization
Monomers added together through multiple addition reactions Examples:

Examples Pg 83: Table 2.1

 monomers are joined together by the formation of ester or amide bond Water created as a side product Example:

CONDENSATION Polymerization

Polyesters contain many ester bonds Nylon (polyamide) contains many amide bonds

HOMEWORK
Page 63: 1-4 Page 64: 1-5 Page 67: 5-8 Page 73: 9-13 Page 78: 14-17 (See CONCEPT Organizer) Page 79: 1-8