2) Organic Reactions 2.1- 2.3.ppt
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Transcript of 2) Organic Reactions 2.1- 2.3.ppt
7/27/2019 2) Organic Reactions 2.1- 2.3.ppt
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REACTIONS OFORGANIC
COMPOUNDS
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1) Addition2) Substitution
3) Elimination
4) Oxidation5) Reduction
6) Condensation
7) Hydrolysis
Types of SubstitutionReactions
She called it
a Blood Bath!
I wonder whyshe wrote it in
Japanese
Look! I think
she’s using it to
blow her nose
Whew! That
was easy!
MAIN TYPES OF REACTIONS inOrganic Chem (not reactions to your last test!)
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1) ADDITION REACTION•Atoms added to a double or triple bond
•Alkene or Alkyne undergoes addition reactionto break a double or triple bond
•Example:
Reactant XY added to alkene makes alkane
To recognize: Two reactants make 1 product
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1) ADDITION REACTIONS
Common atoms that can be added toan 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)
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EXAMPLES: Addition Reactions
1)
2)
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ADDITION REACTIONS:ALKENES
• Symmetrical molecule reactswith asymmetrical molecule togive one product.
Symmetrical Asymmetrical
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RULES FOR ADDITION• Two asymmetrical molecules react to
give two products.Example:
Which product is favoured ?
Asymmetrical
Asymmetricalor
+
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Major product
Minor Product
2-bromobutane
1-bromobutane
“MARKOVNIKOV’S” Rule• "the rich get richer"
• The carbon atom with the largest number ofcarbon atoms gets the X (halogen) or OH bind toit
• Therefore 2- bromobutane is favoured
+
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ADDITION REACTIONS:ALKYNES
• Also follow Markovnikov’s rule whenasymmetrical
1,1,2,2-tetrabromopropaneAsymmetrical
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ADDITION REACTIONS:ALKYNES
• May occur as two addition reactions:
+
+
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2) SUBSTITUTION REACTION
• A hydrogen atom or functional group isreplaced by a different functional group
• To recognize: two compounds react to formtwo products.
2-butanamine2-bromobutane
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2) SUBSTITUTION REACTION
1) CH3CH2-OH + HI CH3CH2-I + H2O
2)
3)
ethanol iodoethane
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SUBSTITUTION REACTIONAromatics
• Aromatics can only undergo substitutionreactions
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SUBSTITUTION REACTIONAlcohols
• Halogens in HCl, HBr or HI can substitutethe OH group of alcohol or the reverse.
• For Ex:
CH3-CH2-OH + HCl CH3-CH2Cl + H2O
• The reverse reaction:
CH3-CH2Cl + OH-
CH3-CH2-OH + Cl-
(from water)
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3) ELIMINATION REACTION• atoms are removed form a molecule to form
double bonds.• Reverse of addition
• To recognize: One reactant breaks into two
products
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ELIMINATION REACTION:Alcohol
• undergo elimination when heated in presenceof strong acids, for example: H2SO4
Example:
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ELIMINATION REACTION:Alkyl Halides
• Undergo elimination to produce alkenes
Bromoethane ethene hydrobromic acid
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4) OXIDATION &5) REDUCTION REACTIONS
• Change in the number of H or O atomsbonded to C
• Always occur together• One reactant is oxidized while the
other is reduced
• For now, lets focus on reactant only…
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4) OXIDATION
• Carbon atom forcesmore bonds to Oxygenor less to Hydrogen
• For example: formation
of C=O bond• Occurs in presence of
oxidizing agents [O]such as KMnO
4, K
2Cr
2O
7,
and O3
• For now, focus onorganic reactant only
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4) OXIDATION:Alcohol
• Alcohol oxidation can form an aldehyde orketonePrimary Alcohol
Secondary Alcohol
Tertiary Alcohols do not oxidize
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4) OXIDATION:Aldehyde
• Aldehydes undergo oxidation to producecarboxylic acid
Example:
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5) REDUCTION REACTION
• Carbon atom forms fewer bonds toOxygen 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 whereHydrogen [H] is added
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5) REDUCTION:Alkene
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5) REDUCTION:Aldehyde/Ketone
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6) CONDENSATION
• two molecules combine to form a single, biggermolecule.
• 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 anamide
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7) HYDROLYSIS• 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
1-propanol
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POLYMERS
• very long molecules made by linking small moleculescalled monomers
• Example:
-PET(Polyethylene terephthalate ) polymers
- Plastics are polymers that can be heated and mouldedinto specific shapes and forms
-Polyethene is made from monomer of
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POLYMERS
can be synthetic or natural• Synthetic polymers
– man made polymer like plastics and polyester
• Natural polymers– found in nature like glucose
and silk
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ADDITION Polymerization
• Monomers added together through multipleaddition reactions
• Examples:
• Examples Pg 83: Table 2.1
CONDENSATION
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CONDENSATIONPolymerization
• monomers are joined together by the formation ofester or amide bond
• Water created as a side product
• Example:
• Polyesters contain many ester bonds
• Nylon (polyamide) contains many amide bonds