Alcohols

1
Alcohols

• 1. Addition of OH group to alkene produces
  alcohol
• ethanol 2-propanol

2
Alcohol Nomenclature

• 1. Longest C chain with -OH is parent chain
• 2. Replace -e in parent name with -ol
• 3. End nearest -OH is C1
• 4. Number name side groups appropriately

3
Alcohol Examples

• 4-methyl-2-pentanol
• 3-chloro-2-butanol

4
Cycloalcohols

• 1. Addition of -OH group to cycloalkene produces
  cycloalcohol
• 2. Carbon with -OH is C1
• 3. Number side groups to give lowest values

5
Cycloalcohol Examples

• cyclohexanol
• 
  3-methylcyclohexanol

6
Diols Triols

• 1. Diol- alcohol with 2 -OH groups
• 1,2-ethanediol
• 2. Triol- alcohol with 3 -OH groups
• 1,2,3-propanetriol (glycerol,
  glycerine)

7
Alcohol Solubility

• 1. -OH group is polar
• 2. Short chain alcohols are water soluble,
  methanol to n-butanol
• 3. Long chain alcohols are water insoluble,
  n-pentanol on up

8
Phenols

• 1. Addition of -OH group to benzene produces
  phenol
• phenol (carbolic acid)
• 
  4-chlorophenol (p-chlorophenol)

9
Phenol Synthesis
10
Phenol Properties

• 1. Ionizes in H2O as weak acid
• 2. Conc phenol is corrosive, weak solns were
  used antiseptically

11
Thiols

• 1. Addition of -SH group to organic compound
  produces thiol
• 2. Similar solubilty as alcohols
• 3. Many have strong odors
• 4. Ethanethiol added to methane for detection

12
Thiol Nomenclature

• 1. Longest chain with -SH is parent chain
• 2. Number parent chain to give lowest value to C
  with -SH group
• 3. Mercaptan- older term for thiol

13
Thiol Examples

• ethanethiol
  2-propene-1-thiol
• trans-2-butene-1-thiol

14
Ethers

• Two carbon chains attached by single bonds to O
• 2. Chains may be alkyl, aromatic, or one of each
• 3. Slight polarity, relatively nonreactive,
  solvents
• 4. Vapors can react explosively with oxygen

15
Naming Ethers, IUPAC

• Name shorter chain, replace -ane suffix with
  -oxy
• 2. Write name of longer chain
• 3. Number from short to long chain starting at
  long chain
• 4. Write number of -oxy carbon followed by dash
  and name

16
Naming Ethers, common

• Used for many simple ethers
• 2. Alkyl or aromatic in alphabetical order
  followed by ether

17
Ether Examples 1

• 1-methoxypropane (1-methyl propyl ether)
• 2-methoxybutane (2-methyl butyl ether)

18
Ether Examples 2

• ethoxybenzene (ethyl phenyl ether)
• phenoxybenzene (diphenyl ether)

19
Ether Solubilty

• 1. Oxygen atom makes ethers slightly polar, not
  as polar as alcohols
• 2. Short chain ethers are more soluble in H2O
  than longer chains
• 3. Longer chain ethers are insoluble in H2O

20
Alcohol Reactions

• 1. Combustion
• 2. Dehydration

21
Alcohol Combustion

• Alcohols combine with O2 combust, needs
  activation energy

22
Alcohol Dehydration , T

• 1. Produces alkene H2O, high heat H catalyst
  

23
Alcohol Dehydration , T

• 1. Produces ether H2O, low heat H catalyst

24
Carbonyl Group

• 1. C joined to O with double bond
• 2. Aldehydes- C in carbonyl attached to at least
  one H
• 3. Ketones- C in carbonyl attached to two other C

25
Aldehyde Examples

• methanal
  ethanal
• (formaldehyde)
  (acetaldehyde)
• phenylmethanal
• (benzaldehyde)

26
Aldehyde Nomenclature

• 1. Longest C chain with carbonyl group is parent
  chain, change -e to -al
• 2. C with aldehyde group is C1
• 3. Common names are often used for unbranched
  aldehydes with one to four carbons

27
Aldehyde Nomenclature Examples

• 2-hydroxypropanal
• 
  4-chlorobenzanal
• 
  (4-chlorobenzaldehyde)

28
Ketone Examples

• propanone
• (dimethyl ketone)
• (acetone)
• 
  butanone
• (ethyl
  methyl ketone)
• 
  (MEK)

29
Ketone Nomenclature

• 1. Longest C chain with carbonyl group is parent
  chain, change -e to -one
• 2. End C in shorter chain is C1
• 3. Common names are often used, alphabetize alkyl
  groups

30
Ketone Nomenclature Examples

• 4-methyl-2-pentanone
• 
  5-chloro-2-pentanone

31
Aldehyde Ketone Solubility

• 1. Carbonyl group is polar
• 2. Short chain aldehydes ketones, C1 to C4, are
  water soluble

32
Oxidation Reduction

• 1. Oxidation- Always loss of e- by loss of 2H
  atoms /or gain of O atom
• 2. Reduction- Always gain of e-by gain of 2H
  atoms /or loss of O atom

33
Alcohol Classification

• 1. Primary alcohol, 1o- 1 alkyl group or hydrogen
  attached to C-OH
• 2. Secondary alcohol, 2o- 2 alkyl groups attached
  to C-OH
• 3. Tertiary alcohol, 3o- 3 alkyl groups attached
  to C-OH

34
1o, 2o, 3o Alcohol Examples

• ethanol
  2-propanol
• 1o alcohol
  2o alcohol
• 2-methyl-2-butanol
• 3o alcohol

35
1o Alcohol Oxidation

• Oxidation of 1o alcohol first produces aldehyde
• ethanol oxidizing ethanal
• agent
  (acetaldehyde)

36
Aldehyde Oxidation

• Oxidation of aldehyde produces carboxylic acid
• methanal oxidizing
  methanoic acid
• (formaldehyde) agent
  (formic acid)

37
2o Alcohol Oxidation

• 1. Oxidation of 2o alcohol produces ketone
• 2-propanol oxidizing propanone
• agent
  (acetone)
• 
  (dimethyl ketone)
• 2. 3o alcohols do not oxidize

38
Aldehyde Reduction

• 1. Reduction of aldehyde produces 1o alcohol
• propanal
  1-propanol

39
Ketone Reduction

• 1. Reduction of ketone produces 2o alcohol
• propanone
  2-propanol
• (acetone)
• (dimethyl ketone)

40
Hemiacetal

• 1. Alcohol and aldehyde produce hemiacetal
• 2. Left rxn, so hemiacetal is hard to obtain
• ethanal methanol hemiacetal

41
Hemiketal

• 1. Alcohol and ketone produce hemiketal
• 2. Left rxn, so hemiketal is hard to obtain
• propanone methanol hemiketal