chapter 2: reactions of organic compounds. 1)addition 2)substitution 3)elimination 4)oxidation...
TRANSCRIPT
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CHAPTER 2: REACTIONS OF
ORGANIC COMPOUNDS
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1) Addition2) Substitution3) Elimination4) Oxidation5) Reduction6) Condensatio
n7) Hydrolysis8) Combustion
Types of Substitution Reactions
She called it a Blood Bath!
I wonder why she wrote it in Japanese
Look! I think she’s using it to blow her nose
Whew! That was easy!
MAIN TYPES OF REACTIONS in Organic Chem
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1) ADDITION REACTION •Atoms added to a double or triple bond•Alkene or Alkyne undergoes addition reaction to break a double or triple bond•Example:
Reactant XY added to alkene makes alkaneTo recognize: Two reactants make 1 product
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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)
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EXAMPLES: Addition Reactions
1)
2)
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ADDITION REACTIONS: ALKENES
•Symmetrical molecule reacts with asymmetrical molecule to give 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
Asymmetrical
or+
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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 of
carbon atoms gets the X (halogen) or OH bind to it
• Therefore 2- bromobutane is favoured
+
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ADDITION REACTIONS: ALKYNES
• Also follow Markovnikov’s rule when asymmetrical
1,1,2,2-tetrabromopropane
Asymmetrical
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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 is
replaced by a different atom or functional group
• To recognize: two compounds react to form two 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 substitution reactions
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SUBSTITUTION REACTIONAlcohols
• 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 + 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 presence of 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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Elimination
• If an asymmetrical molecule undergoes an elimination reaction, constitutional isomers can form example #3
• General rule: H atom most likely to be removed from C atom with most C-C bonds
• “The poor get poorer!” – opposite of Markovnikov’s Rule
– Called Zaitsev’s rule
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Elimination
(major product)
(minor product)
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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…
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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
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4) OXIDATION: Alcohol
• Alcohol oxidation can form an aldehyde or ketone
Primary Alcohol
Secondary Alcohol
Tertiary Alcohols do not oxidize
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4) OXIDATION: Aldehyde
• Aldehydes undergo oxidation to produce carboxylic acid
Example:
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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/Pt
where Hydrogen [H] is added
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5) REDUCTION:Alkene
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5) REDUCTION:Aldehyde/Ketone
+ [H]
O
R1
C
R2
H
O
R1 C R2
HAldehyde or ketone Reducingagent
alcohol
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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
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Condensation
carboxylic amine amide wateracid
R1
O
O
C
H
+R3
R2
NH + OHH
R1
O
C
R3
R2
N
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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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8) Combustion
• Type of reaction in which a compound reacts with oxygen to produce the oxides of elements that make up the compound
• 2 types:1) Complete combustion: an excess of
oxygen reacts with a hydrocarbon and produces carbon dioxide and water vapour, and releases energy
2) Incomplete combustion: reaction that occurs when insufficient oxygen is present; all elements in the fuel will not combine with oxygen to the greatest extent possible
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Combustion
• Example #1CxHy + O2(g) CO2(g) + H2O(g)
+ energy
• Example #2HC + O2(g) C(s) + CO(g) + CO2(g) + H2O(g) +
energy
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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
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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 multiple
addition reactions• Examples:
• Examples Pg 83: Table 2.1
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CONDENSATION Polymerization
• monomers are joined together by the formation of ester or amide bond
• Water created as a side product• Example:
• Polyesters contain many ester bonds• Nylon (polyamide) contains many amide bonds