Download - Organic chemistry B Chapter 13 Ali phatic cyclic compounds Alicyclic compounds By Prof. Dr
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Organic chemistry BChapter 13
Aliphatic cyclic compoundsAlicyclic compounds
By Prof. Dr.Adel M. Awadallah
Islamic University of Gaza
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• Cycloalkanes: Nomenclature
Cyclopropane Cyclobutane Cyclopentane Cyclohexane
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OH
OH CH3
Br
OH
OH
Bicyclo[2.2.1]heptane Bicyclo[2.2.2]octaneBicyclo[2.1.1]hexane
Bicyclo[2.2.2]octa-2-ene Tricyclo[2.2.2.02,6]octaneTricyclo[2.2.1.02,6]heptane
Cyclopentanol 1,3-Cyclopentadiene 3-Ethylcyclopentene
2-Cyclohexenol 1-Bromo-3-methylcyclohexane 1,3-Cyclohexanediol
Norbornane
1 2
3
45
6
7
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Industrial source
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Preparation
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Reactionssimilar to that of alkanes (free radical substitution) ,
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Reactionsalkenes (addition or cleavage of the double bond)
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Ring Strain in Cyclopropane• Average heat of composition per CH2 = 157.4 Kcal / mol• Ring strain in cyclopropane = 27.6 Kcal/mol• Ring strain in cyclobutane = 26.3 Kcal/mol
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Ring Strain in Cyclopropane
• Eclipsing (torsional) strain: • Strain resulting from deviation
from the staggered arrangement
• Bond-Angle Strain:• Strain resulting from deviation
from the normal bond angle (tetrahedral 109.5)
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Addition to cyclopropane
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Addition to cyclopropaneCyclobutane undergoes hydrogenation under vigorous conditions
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Relieve of torsional strain in cyclobutanePuckered structure (butterfly)
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Relieve of torsional strain in cyclopentaneEnvelope (half chair) structure
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• Conformations of Cyclohexane
CH3H
CH3
H
flip
Chair conformation
Boat conformation
axial
equatorial
flip
5% 95%
flip
0% 100%
methylcyclohexane tert-butylcyclohexane
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Conformations of cyclohexane
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Twist boat is more stable than the boat conformation
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1,2 + 1,4 Trans diaxial or diequatorial1,3 cis diaxial or diequatorial
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Example