alkenes notes
TRANSCRIPT
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Chapter 12
Nomenclature Of Alkenes
ALKENES
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12.1: Structure of Alkenes Describe alkenes as unsaturated hydrocarbon with general
formula of CnH2n, n>2,(C2- C10). 12.2: Nomenclature of alkenes Draw the structures and name the compounds according to
the IUPAC nomenclature for:
i. Straight chain (C2- C10)ii. Branched alkenes (C4- C10)iii. Cyclic alkenes (C4-C6)
LEARNING OUTCOMES
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Contain at least one carbon–carbon double bond.
Unsaturated hydrocarbon.
Old name: olefin.
General formula CnH2n
Name derived from alkane by changing the suffix from ‘ane’ to ‘ene’.
INTRODUCTION TO ALKENES
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NOMENCLATURE OF ALKENES
STEP 1
Find the longest carbon chain containing C═C.
Name the parent hydrocarbon.
correctC C
H
H
CH3CH2
CH3CH2CH2
C C
H
H
CH3CH2
CH3CH2CH2
named as pentene
not as hexene
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NOMENCLATURE OF ALKENESSTEP 2
Begin at the end nearer the C═C.
Number the C atoms in the chain.
If C═C is at same distance from the two ends, begin at the end nearer to the first branch point.
CH3CH2CH2CH CHCH3
123456
CH3CHCH CHCH2CH3
CH3
1 2 3 4 5 6
Make sure C═C get the lowest possible number!
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NOMENCLATURE OF ALKENESSTEP 3
Number the substituents according to their position in the chain, and list them alphabetically.
Write the full name.
CH3CH2CH2CH CHCH3
123456
2–hexene or hex–2–ene
CH3CHCH CHCH2CH3
CH3
1 2 3 4 5 6
2–methyl–3–hexeneor
2–methylhex–3–ene
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NOMENCLATURE OF ALKENES
3- heptene
C C
CH3
CH3
CH3CH2
CH2CHCH3
CH3
1
3
2
6
4
5 7
Name : 3,4,6 - trimethyl – 3 - heptene
3-methyl 6-methyl4-methyl
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NOMENCLATURE OF ALKENES
CH2C
CH2CH3
CH2CH2 CH2 CH2CH3
1
3
2
64 5 7
Name : 2 – ethyl - 1 - heptene
2-ethyl
CH2C
CH2CH3
CH2CH2 CH2 CH2CH3
12
3
4 5 6 7 8
not as 3 -octene
named as
correct
1-heptene1-heptene
CH2C
CH2CH3
CH2CH2 CH2 CH2CH3
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NOMENCLATURE OF ALKENES
1- hexene
1 32 64 5
Name : 3 - isopropyl - 2,5 – dimethyl-1-hexene
2-methyl 3-isopropyl5-methyl
CH2 C
CH3
CH2CH2CHCH3
CH
CH3
CH3
CH3
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NOMENCLATURE OF CYCLOALKENES
Cycloalkenes are named similarly as acyclic alkenes, but number the cycloalkenes so that the C═C is between C1 and C2 and the first substituent has the lowest number possible.
CH31
2
3
4
56
1–methylcyclohexene
If there is only one C═C, no need to indicate the position of C═C !
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NOMENCLATURE OF CYCLOALKENES
1
2
3
4
56
1,4– dimethylcyclohexene
CH3
CH31
23
4
5
1,5–dimethylcyclopentene
CH3
CH3
Cycloalkenes are named similarly, but number the cycloalkenes so that the C═C is between C1 and C2 and the first substituent has the lowest number possible.
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NOMENCLATURE OF ALKENES
cyclobutene
1
3 2
4
Answer : 1,3 - dimethylcyclobutene
1 - methyl 3 - methyl
CH3
CH3
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NOMENCLATURE OF ALKENES
propene
13 2
Name : 3 - cyclopropylpropene
3 - cyclopropyl
CHCH CH2
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EXERCISE - 1
Give IUPAC names for the followingcompounds:
a)
H2C CCCH3
H3C CH3
CH3
b)
CH3CH2CH CCH2CH3
CH3
c)
CH3CHCH
CH3
CHCHCH3
CH3
d)CH3CHC CCH2CH3
CH3
CH3
CH3
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EXERCISE - 2
Give the structures and the IUPAC namesfor all alkenes with molecular formula of C6H12,ignoring cis-trans isomer.(Hint: There are 13.)
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EXERCISE - 3
Name the following compounds:
a) b)
c)
CH3CH CCH2CH3
CH2CH3CH3
CCH2CH3
CCH2CHCH3H2C
CH3CH3
CCH2CH2CH3
CH2
CH2CH2
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EXERCISE - 4
Name the following compounds:
a) CH3 b) c)
d) e)
CH3
CH3CH3
CH3
CH3
CH3
CH3
CH2CH3
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Restricted rotation of carbon-carbon bonds due to:
presence of C═C.
Two different atoms or group of atoms attached to each of C atoms which form double bond.
CIS–TRANS ISOMERISM
C C
H
CH3
H3C
H
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EXAMPLE: CH3CH═CHCH3
2–butene
C C
H
CH3
H3C
H
trans–2–butene
C CH
CH3H3C
H
cis–2–butene
Two groups on the same side cis
Two groups on opposite side trans
CIS–TRANS ISOMERISM ON C═C
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EXERCISE - 5
Determine which of the following compoundsshow cis-trans isomerism.Draw and name the cis and trans isomers ofthose that do.
a) 3–hexeneb) 3–methyl–2–pentenec) 2,3–dimethyl–2–pentene
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Which of the following compounds can exist as pairs of cis-trans isomers?Draw each cis–trans pair.
a) CH3CH═CH2
b) (CH3)2C═CHCH3
c) CH3CH2CH═CHCH3
d) (CH3)2C═C(CH3)CH2CH3
e) ClCH═CHClf) BrCH═CHCl
EXERCISE - 6
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EXERCISE - 7
Give the structural formula of the following compound and indicate cis-trans isomer: • 2,3–dimethyl–2–butene• cis–2–methyl–3–heptene• 3,6–dimethyl–1–octene• 3–chloropropene• 2,4,4–trimethyl–2–pentene• trans–3,4–dimethyl–3–hexene
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EXERCISE - 8
Menthene, a hydrocarbon found in mint plants, has the systematic name as 1–isopropyl–4–methylcyclohexene.Draw its structure.
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EXERCISE - 9
Each of the following name is incorrect.Give the correct name
a) 4,7–dimethyl–4–octeneb) 5–bromo–3–methyl–3–hexenec) 2,3–dichlorocyclohexened) 4–ethyl–2–cyclohexenee) 7–bromo–5–ethyl–2–methyl–4–octenef) 3–bromo–6–chloro–5–methylcyclohexeneg) 3–propyl–1–cyclopenteneh) 3–chloro–2–methylcyclobutene
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EXERCISE - 10
Each of the following name is incorrect.Draw the structure represented by the incorrectname (or a consistent structure if the name is ambiguous) and give your drawing the correct name:
a) cis–2,3–dimethyl–2–penteneb) 2–methylcylopentenec) 3,4–dimethylcyclohexened) cis–2,5–dibromo–3–ethyl–2–pentene
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12.3: Preparation of alkenes
a. Show the preparation of alkenes through dehydration of alcohols.
b. State Saytzeff’s rule.
c. Predict the major product using Saytzeff’s rule
LEARNING OUTCOMES
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By elimination reactions:
Dehydration
loss of H2O from alcohol
Latin: “de” means down, away, removal
PREPARATION OF ALKENE
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C C
H OH
acid , heat+C C H2O
Reactant: alcohol.
Conditions:
Concentrated H2SO4 or other strong acids
Heat
H and OH eliminated!
DEHYDRATION OF ALCOHOLS
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SAYTZEFF’S RULE
An elimination occurs to give the major product,which is the most highly substituted alkene.
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EXAMPLE: dehydration of 2–butanol
CH3
OH
CH2 CH3CH – H+
2–butene
1–butene
major product
minor product
– H2O
CH3
CH
C
CH3
H
CH3CH2
CH
C
H
H
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EXAMPLE: dehydration of 3,3–dimethyl–2–butanol
– H2O
OH
CH3–C–CH–CH3
CH3
CH3
– H+
major
minor
C
CH3H3C
C
H3C CH3
C
CH3HC
H CH(CH3)2
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EXERCISE - 11
Predict the major products of dehydrationof the following alcohols:
a) 2–pentanolb) 1–methylcyclopentanolc) 2–methylcyclohexanol
Note: naming cycloalcohols:C where the OH group is attached shouldbe numbered as C1
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EXERCISE - 12
Give the products that would be formedwhen each of the following alcohols issubjected to acid-catalyzed dehydration.If more than one products would be formed,designate the alkene that would be the majorproducts. (Neglect cis-trans isomerism).
a) 2–methyl–2–propanolb) 3–methyl–2–butanolc) 3–methyl–3–pentanold) 2,2–dimethyl–1–propanole) 1,4–dimethylcyclohexanol
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12.4: Reaction of alkenes:
a) Explain the addition reactions of alkenes with:
i. Hydrogen in the presence of catalyst.
ii. Halogen (Cl2 or Br2) in inert solvent (CH2Cl2)
iii. Hydrogen halides (HCl and HBr)
b) Introduce Markonikov’s rule for reaction (iii)
LEARNING OUTCOMES
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REACTION OF ALKENES
C C + A—B addition C C
BA
A–B can be:
hydrogen H2 in catalyst
hydrogen halides H–X
halogen in inert solvent X2 in CH2Cl2
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HYDROGENATION OF ALKENE
alkane
C C + C C Ni, Pd or Pt
H H
alkene
The addition of H2 to a double bond
Alkane is formed
HH
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HYDROGENATION OF ALKENE
EXAMPLE:
+Ni, Pd or Pt
C═C
H3C CH3
H H
H H H3C C C CH3
H H
cis-2-butene butane
HH
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HALOGENATION OF ALKENE IN INERT SOLVENT
Alkenes reacts rapidly with Cl2 and Br2 in inert solvents such as CH2Cl2 or CCl4
EXAMPLE:
CH3CH═CHCH3 +CH2Cl2
2,3–dichlorobutane
C—CCH3CH3
HH
Cl ClCl Cl
2-butene
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HALOGENATION OF ALKENE IN INERT SOLVENT
EXAMPLE:
+CH2Cl2
1,2–dichloropropane
+ CCl4
1,2–dibromocyclopentane
C—CH CH3
HH
Cl ClC—CH CH3
HH
Cl Cl
Br BrBr Br
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HYDROHALOGENATION OF ALKENE
H–X: HBr and HCl
C C + H C CX
alkenehaloalkene
XH
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HYDROHALOGENATION OF ALKENE
EXAMPLE:
+
2-butene 2–bromobutane
H BrC CCH3 CH3
HH
C CCH3 CH3
HH
BrH
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HYDROHALOGENATION OF ALKENE
EXAMPLE:
+
2-methyl-2-butene2–chloro-2-methylbutane
H ClC CCH3 CH3
CH3HC CCH3 CH3
CH3H
ClH
For unsymmetrical alkene?
why H choose here ?
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MARKOVNIKOV’S RULE
Vladimir Vassilyevich Markovnikov (1838-1904). Russian chemist.
In addition of HX to an unsymmetrical alkene, H atom adds to the C atom of the double bond that already has the greater number of H atoms.
CH2 CH3CH
C atom with the greater number of
H atoms
H Br
CH2 CH3CH
H Br
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EXAMPLE:
+
2–chloro–2–methylbutane
CH3–CH–C═C
CH3
H
H H Cl
CH3–CH2–C
CH3
Cl
C H
H
H
C atom with the greater number of
H atoms
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EXERCISE - 13
What product would you expect from reactionof HCl with:
a) 1–ethylcyclopenteneb) 1–methylcyclohexene
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EXERCISE - 14
Suggest the possible alkene that can be used toprepare 3-chloro-3-methylhexane.There may be more than one possibility.
? CH3CH2CCH2CH2CH3
CH3
Cl
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EXERCISE - 15
Predict the products of the following reactions:
a)
b)
+ HCl ?
(CH3)2C═CHCH2CH3+ HBr ?
c) CH3CH2CH2CH═CH2 + HBr ?
d) + HBr ?CH2
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EXERCISE - 16
What alkenes would you start with to preparethe following compounds?
a) Bromocyclopentane
b) CH3CH2CHBrCH2CH2CH3
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EXERCISE - 17
Predict the products of the following reactions:
a)
b)
c)
d)
CH3CH2CH═CCH2CH3
CH3
+ HCl ?
1–ethylcyclopentene + HBr ?
2,2,4–trimethyl–3–hexene + HBr ?
+ HBr ?
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12.5: Unsaturation test for alkenes
Explain the unsaturation test for alkenes:
i. Baeyer’s test using dilute, alkaline solution of KMnO4 at room temperature.
ii. Reaction with bromine in CCl4.
LEARNING OUTCOMES
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UNSATURATION TEST FOR ALKENE
to test the presence of C=C. to distinguish alkane and alkene (or alkyne).
BROMINE TEST BAEYER TEST
12.5
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CCl4CCl4
Observation: Red–brown color of Br2 dissappear (colorless) almost instantly.
BROMINE TEST
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BROMINE TEST
Alkanes do not react with Br2 or Cl2 at room
temperature and in the absence of light.
R—H
alkane
+ Br2room temperatureIn the dark , CH2Cl2
no appreciablereaction
Observation:The color bromine unchanged.
R—Halkane
+ Br2 bromoalkaneslight
Observation:The colour of bromin dissappears.
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BAEYER TEST
C═C is oxidized dihydroxylation
C C
OH OH
+C C KMnO4
diol
dilute / cold OH-
EXAMPLE
CH3CH═CHCH3 + KMnO4dilute / cold OH-
decolouration: purple colourless
CH3CH—CHCH3
OH OH2,3–butanediol
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EXAMPLE
CH3CH═CH2 + KMnO4
dilute / cold OH-
CH3CH—CH2
OH OH1,2–propanediol
propene
OH
OH
+ KMnO4
cyclohexene 1,2–cyclohexanediol
BAEYER TEST
dilute / cold OH-
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EXERCISE - 17
Show the structures of alkenes that give the following products on reaction with cold, dilute alkaline solution of KMnO4:
CH3CH2CH═CH2 a)
b)
c) (CH3)2C═CHCH3
(CH3)2C═CHCHC(CH3)2
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EXERCISE - 18
Write the structural formula for the productsthat is formed when 1–butene reacts with each of the following reagents:
a) HCIb) H2, Ptc) Br2 in CH2Cl2
d) cold dilute KMnO4, OH-
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EXERCISE - 19
Repeat EXERCISE using cyclobutene instead of 1–butene.
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END OF SLIDE SHOW