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7/28/2019 1c Stdnt Chapter 4 ORGANIC CHEMISTRY - Hydroxyl
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CHAPTER 4: ORGANIC CHEMISTRY
ALCOHOLS
HYDROXY
COMPOUNDS
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v
q
OH
qOH orO
q
OH
OH
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H
C
H
OHH3C
CH3
C
H
OHH3C
CH3
C
CH3
OHH3C
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Naming Alcohols
CH CH CH CH CHCH OH
Give the IUPAC name of thealcohol:
CH2CH2CH3C
C
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CH3OH CH3CH2OH
CH3CH2CHCH3
OHC
CH3
CH3H3CCH3CHCH2OH
CH3
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H2C CH2
OHOH
H2CHC CH2
OHOHOH
H3CHC CH2
OHOH
H3CH2C
HC
H2C CH2
OHOH
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H2C CH
H2C OH H C C
H2C
H2C
H2C OH
2-propen-1-ol4-pentynol
H3C CH
CH
2C
2C OH HOH2C
H
H
CH2CH2CH3
c c
c c
trans-2-hexen-1-ol
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OH OH
NO2
OH
CH3
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Reactions of Alcohols
CH3OH + HBr CH3Br + H2OH+
**Substitution reactions may be used toconvert an alcohol to a haloalkane
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q
(CH3)3COH + HCl (CH3)3CCl + H2Oroom temperature
C2H5OH + HCl(g) C2H5Cl + H2OZnCl2
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reflux
2 5 3 2 5 3 3 3
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2P + 3Br2 2PBr3
3C2H5OH + PBr3 3C2H5Br + H3PO3
6C2H5OH + 2P + 3Br2 6C2H5Br + 2H3PO3
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2 3
3C2H5OH + PI3 3C2H5I + H3PO3
6C2H5OH + 2P + 3I2 6C2H5Br + 2H3PO3
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C2H5OH + PCl5 C2H5Cl (POCl3) + HCl
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C3H7OH + SOCl2 C3H7Cl + SO2 + HClreflux
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R C C H
H H
H OH
R C C H
H H
+ H2Oexcess conc. H2SO4, 170
oC
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Sayt effs rule.
**Dehydration can be used to convert alcohols toalkenes
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H C CHCH2CH3
H
H OH
H2C CHCH2CH3 + H2O
H3CHC C CH3
H
H
H3CHC CHCH3 + H2O
OH (2 alkyl groupsattached to the double bond)
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Saytzeffs rule: For elimination reaction thatproduces more than one alkenes, the alkene withmore than one alkyl substituents in the doublebond is the predominant product.
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OH 1-pentene (minor product)
2-pentanol 2-pentene (major product)
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H H
+ H2OR C C H
H OH
H2C CH2
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OH 85 % H3PO4, 165-170oC
+ 2
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CH3CH2OH CH2 CH2 + H2O2 3
heat
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The ease of dehydration follows
the order:
OH
R
R OH
R
H OH
H
R
>>
R R H
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Cannot be oxidi ed
KMnO4K2Cr2O7
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Finalproduct
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CH3(CH2)5CH2OH + [O] CH3(CH2)5CHO + H2OPCC
CH2Cl2, 25oC
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OH
H2CrO 4
O
Cyclopentanol
(secondary alcohol)
cyclopentanone
O HH 2C rO 4
O
H
H 2C rO 4
O H
O
Butanol (primary alcohol)butanal
butanoic acid29
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q
sodiumalkoxides) hydrogen gas
CH3OH + Na CH3ONa + H2CH3OH + K CH3OK + H2
potassium methoxide
q
q
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Lucas Reagent Test
OH ClZnCl2/ HCl
2-methyl-2-butanol 2-chloro-2-methylbutane
(30 alcohol) (Cloudiness appears immediately)
*Cloudiness isdue to theformation ofalkyl halide
ZnCl2/ HCl
OH Cl2-pentanol 2-chloropentane(20 alcohol) (cloudiness appears in a few minutes)
OH No reactionpropanol (10 alcohol)
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Only 10 and 20 alcohols are oxidised by hot acidifiedKMnO4 or hot acidified K2Cr2O7 solution.
10 and 20 alcohols decolourise the purple KMnO4solution,
whereas the colour of the K Cr O solution chan esfrom orange to green.
No reaction for 30 alcohols.
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q
H3C
H
q I2/ NaOH))
OH
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H3C C R
H
OH
+ 4I2 + 6NaOH CHI3 + RCOONa + 5NaI + 5H2O
CH3CH2OH I2/ NaOH CHI3Triiodomethane (iodoform)yellow precipitate
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H H
H3C C H
OH
H C H
OH
H3C C CH3
H
OH
CH3CH2CH2OH
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Summary
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