alcohols, amines, ethers and epoxides: chapter 10
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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
Chapter 10 1
Alcohols, Amines, Ethers and Alcohols, Amines, Ethers and Epoxides:Epoxides:Chapter 10Chapter 10
Chapter 10 2
Contents of Chapter 10 Naming Alcohols Substitution and Dehydration of
Alcohols Oxidation of Alcohols Naming Ethers Epoxides
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.
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
Chapter 10 5
Examples
Chapter 10 6
Conversion of Alcohols to Alkyl Halides
Hydrogen halide reactions can be SN1 or SN2
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
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
Chapter 10 9
Dehydration of Alcohols
Zaitsev’s Rule is followed whenever possible
Chapter 10 10
Dehydration of Alcohols
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
Chapter 10 12
Cr6+ Oxidation of Alcohols
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
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
Chapter 10 15
Epoxides