Chapter 3 Alcohols Phenols Ethers Thiols Lecture PLUS

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Chapter 3 Alcohols, Phenols, Ethers, Thiols Lecture. PLUS Timberlake 1

Chapter 3 Alcohols, Phenols, Ethers, Thiols Lecture. PLUS Timberlake 1

3. 1 Organic Compounds with Oxygen Atoms sp 3 . . -O. . Alcohols

3. 1 Organic Compounds with Oxygen Atoms sp 3 . . -O. . Alcohols and ethers (Chp 3) or . . O=. . sp 2 Aldehydes and ketones (Chp 4), amides (Chp 6) BOTH KINDS OF OXYGEN ATOMS IN Carbohydrates (Chp 7), carboxylic acids and esters (Chp 5) Lecture. PLUS Timberlake 2

3. 2 Organic Compounds with Oxygen Atoms Derived from water H-O-H sp 3 Alcohols

3. 2 Organic Compounds with Oxygen Atoms Derived from water H-O-H sp 3 Alcohols -OH hydroxyl CH 3 -OH CH 3 CH 2 -OH saturated Lecture. PLUS Timberlake 3

Hydroxy groups have the same molecular shape as water ? ? Bond angle =

Hydroxy groups have the same molecular shape as water ? ? Bond angle = ? Molecular shape = ? Lecture. PLUS Timberlake 4

3. 3 Naming Alcohols n A carbon compound that contain -OH (hydroxyl) group n

3. 3 Naming Alcohols n A carbon compound that contain -OH (hydroxyl) group n In IUPAC name, the -e in alkane name is replaced with -ol. CH 4 methane CH 3 OH methanol (methyl alcohol) CH 3 ethane CH 3 CH 2 OH ethanol Lecture. PLUS Timberlake (ethyl alcohol) 5

More Names of Alcohols n IUPAC names for longer chains number the chain from

More Names of Alcohols n IUPAC names for longer chains number the chain from the end nearest the -OH group. CH 3 CH 2 OH 1 -propanol OH CH 3 CHCH 3 2 -propanol OH CH 3 CHCH 2 CHCH 3 5 -methyl-2 -hexanol Lecture. PLUS Timberlake 6

Name and locate any other substituents present CH 3 OH CH 3 CHCH 2

Name and locate any other substituents present CH 3 OH CH 3 CHCH 2 CHCH 3 5 -methyl-2 -hexanol In cyclic alcohols the –OH is attached to carbon 1 Lecture. PLUS Timberlake 7

In cyclic alcohols the –OH is attached to carbon 1 2 -methylcyclohexanol Naming alcohols

In cyclic alcohols the –OH is attached to carbon 1 2 -methylcyclohexanol Naming alcohols that contain C=C and rings … Lecture. PLUS Timberlake 8

Alcohols with more than one hydroxyl antifreeze HO-CH 2 -OH 1, 2 -ethanediol (ethylene

Alcohols with more than one hydroxyl antifreeze HO-CH 2 -OH 1, 2 -ethanediol (ethylene glycol) OH glycerol HO-CH 2 -CH-CH 2 OH glycerin 1, 2, 3 -propanetriol IUPAC name? Lecture. PLUS Timberlake 9

3. 4 Isomerism in alcohols CH 3 OH CH 3 CHCH 2 CHCH 3

3. 4 Isomerism in alcohols CH 3 OH CH 3 CHCH 2 CHCH 3 5 -methyl-2 -hexanol OH CH 3 CHCH 2 CH 3 5 -methyl-3 -hexanol Lecture. PLUS Timberlake 10

1. Constitutional isomerism 2. Skeletal isomerism 3. Positional isomerism 4. Stereoisomerism Lecture. PLUS Timberlake

1. Constitutional isomerism 2. Skeletal isomerism 3. Positional isomerism 4. Stereoisomerism Lecture. PLUS Timberlake 11

Learning Check Name the following alcohols: A. OH CH 3 CHCHCH 2 CH 3

Learning Check Name the following alcohols: A. OH CH 3 CHCHCH 2 CH 3 OH B. Lecture. PLUS Timberlake 12

Solution Name the following alcohols: A. OH 3 -methyl-2 -pentanol CH 3 CHCHCH 2

Solution Name the following alcohols: A. OH 3 -methyl-2 -pentanol CH 3 CHCHCH 2 CH 3 OH B. cyclobutanol Lecture. PLUS Timberlake 13

3. 5 Common alcohols CH 3 OH CH 3 CH 2 OH methanol OH

3. 5 Common alcohols CH 3 OH CH 3 CH 2 OH methanol OH Isopropyl Alcohol CH 3 CHCH 3 Lecture. PLUS Timberlake rubbing alcohol antiseptic 14

3. 5 Common alcohols (cont. ) ethylene glycol HO-CH 2 -OH (antifreeze) OH glycerol

3. 5 Common alcohols (cont. ) ethylene glycol HO-CH 2 -OH (antifreeze) OH glycerol HO-CH 2 -CH-CH 2 OH propylene glycol (in soap, cosmetics) HO-CH 2 -CH 3 OH (drug formulations, cosmetics) Lecture. PLUS Timberlake 15

Chapter 22 Alcohols Ethers Phenols and Thiols HeinChapter 22 Alcohols Ethers Phenols and Thiols Hein
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