alcohols, amines, ethers and epoxides: chapter 10

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Chapter 10 1 Alcohols, Amines, Alcohols, Amines, Ethers and Epoxides: Ethers and Epoxides: Chapter 10 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 Presentation

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Page 1: Alcohols, Amines, Ethers and Epoxides: Chapter 10

Chapter 10 1

Alcohols, Amines, Ethers and Alcohols, Amines, Ethers and Epoxides:Epoxides:Chapter 10Chapter 10

Page 2: Alcohols, Amines, Ethers and Epoxides: Chapter 10

Chapter 10 2

Contents of Chapter 10 Naming Alcohols Substitution and Dehydration of

Alcohols Oxidation of Alcohols Naming Ethers Epoxides

Page 3: Alcohols, Amines, Ethers and Epoxides: Chapter 10

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.

Page 4: Alcohols, Amines, Ethers and Epoxides: Chapter 10

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

Page 5: Alcohols, Amines, Ethers and Epoxides: Chapter 10

Chapter 10 5

Examples

Page 6: Alcohols, Amines, Ethers and Epoxides: Chapter 10

Chapter 10 6

Conversion of Alcohols to Alkyl Halides

Hydrogen halide reactions can be SN1 or SN2

Page 7: Alcohols, Amines, Ethers and Epoxides: Chapter 10

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

Page 8: Alcohols, Amines, Ethers and Epoxides: Chapter 10

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

Page 9: Alcohols, Amines, Ethers and Epoxides: Chapter 10

Chapter 10 9

Dehydration of Alcohols

Zaitsev’s Rule is followed whenever possible

Page 10: Alcohols, Amines, Ethers and Epoxides: Chapter 10

Chapter 10 10

Dehydration of Alcohols

Page 11: Alcohols, Amines, Ethers and Epoxides: Chapter 10

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

Page 12: Alcohols, Amines, Ethers and Epoxides: Chapter 10

Chapter 10 12

Cr6+ Oxidation of Alcohols

Page 13: Alcohols, Amines, Ethers and Epoxides: Chapter 10

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

Page 14: Alcohols, Amines, Ethers and Epoxides: Chapter 10

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

Page 15: Alcohols, Amines, Ethers and Epoxides: Chapter 10

Chapter 10 15

Epoxides