alcohols, amines, ethers and epoxides: chapter 10
DESCRIPTION
Alcohols, Amines, Ethers and Epoxides: Chapter 10. Contents of Chapter 10. Naming Alcohols Substitution and Dehydration of Alcohols Oxidation of Alcohols Naming Ethers Epoxides. Naming Alcohols. Find longest carbon chain containing the alcohol. - PowerPoint PPT PresentationTRANSCRIPT
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Chapter 10 1
Alcohols, Amines, Ethers and Alcohols, Amines, Ethers and Epoxides:Epoxides:Chapter 10Chapter 10
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Chapter 10 2
Contents of Chapter 10 Naming Alcohols Substitution and Dehydration of
Alcohols Oxidation of Alcohols Naming Ethers Epoxides
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Chapter 10 3
Naming Alcohols Find longest carbon chain containing the
alcohol. OH gives attached carbon lowest possible
number. Break ties with other substituents if
necessary. Substituents are listed in alphabetical order.
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Chapter 10 4
Examples
CH3CH2CH2CH2CHCH2OHCH2CH2CH3
123456
1 2 3
CC
1. Determine longest chain with OHBlue chain is longer; however,Red chain contains OH
2. Name: 2-propyl-1-hexanol
Notice that numbering starts at alcohol group
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Chapter 10 5
Examples
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Chapter 10 6
Conversion of Alcohols to Alkyl Halides
Hydrogen halide reactions can be SN1 or SN2
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Chapter 10 7
Mechanism of SubstitutionSecondary and tertiary alcohols undergo SN1 reaction.
OHH3C
H3CH3C BrH
OH3C
H3CH3C H
H
CH3
H3C CH3
CH2
H3C CH3
Br- HBr
Br
carbocation
tert-butanol
tert-butyl chloride
- H2O
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Chapter 10 8
Mechanism of SubstitutionPrimary alcohols undergo SN2 reaction. Primary carbocations are too unstable to be formed.
OH1-butanol
BrHOH
H
Attack from back-side
OH
H
Br
Br1-bromobutane
- H2O
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Chapter 10 9
Dehydration of Alcohols
Zaitsev’s Rule is followed whenever possible
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Chapter 10 10
Dehydration of Alcohols
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Chapter 10 11
Cr6+ Oxidation of Alcohols
Acidic hexavalent chromium removes all H’s makes C-O bondsPCC removes only one H and makes an aldehyde from a 10 alcohol
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Chapter 10 12
Cr6+ Oxidation of Alcohols
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Chapter 10 13
Nomenclature of Ethers Common Name: Name of alkyl substituents
followed by “ether”O
methyl ethyl ether
O
12
3
1-ethoxy-2-methylpropane
IUPAC
Parent alkyl compound with RO substituent. “-yl” is then replaced by “oxy”
methyl isopropyl etherO
2-methoxy-butaneO1
2
34
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Chapter 10 14
Substitution Reactions of Ethers
Ethers can be cleaved only with HI and HBr, not HCl SN1 and SN2 reactions give opposite regioselectivity;
H goes on bulky C in SN2, and less-hindered in SN1
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Chapter 10 15
Epoxides