ALCOHOLS

Lecture iv
AN INTRODUCTION TO

THE CHEMISTRY
OF ALCOHOLS
 THE CHEMISTRY OF ALCOHOLS
CONTENTS

• Structure and classification of alcohols

• Nomenclature
• Isomerism
• Physical properties
• Chemical properties of alcohols
• Identification using infra-red spectroscopy
• Industrial preparation and uses of ethanol
• Revision check list
 CLASSIFICATION OF ALCOHOLS

Aliphatic • general formula CnH2n+1OH - provided there are no rings

• the OH replaces an H in a basic hydrocarbon skeleton
 CLASSIFICATION OF ALCOHOLS

Aliphatic • general formula CnH2n+1OH - provided there are no rings

• the OH replaces an H in a basic hydrocarbon skeleton

Aromatic • in aromatic alcohols (or phenols) the OH is attached directly to the ring
• an OH on a side chain of a ring behaves as a typical aliphatic alcohol

The first two compounds are

classified as aromatic alcohols
(phenols) because the OH group
is attached directly to the ring.
 CLASSIFICATION OF ALCOHOLS
Aliphatic • general formula CnH2n+1OH - provided there are no rings
• the OH replaces an H in a basic hydrocarbon skeleton

Aromatic • in aromatic alcohols (or phenols) the OH is attached directly to the ring
• an OH on a side chain of a ring behaves as a typical aliphatic alcohol

The first two compounds are

classified as aromatic alcohols
(phenols) because the OH group
is attached directly to the ring.
Structural
differences • alcohols are classified according to the environment of the OH group
• chemical behaviour, eg oxidation, often depends on the structural type

PRIMARY 1° SECONDARY 2° TERTIARY 3°

 NAMING ALCOHOLS
Alcohols are named according to standard IUPAC rules

• select the longest chain of C atoms containing the O-H group;

• remove the e and add ol after the basic name

• number the chain starting from the end nearer the O-H group

• the number is placed after the an and before the ol ... e.g butan-2-ol

• as in alkanes, prefix with alkyl substituents

• side chain positions are based on the number allocated to the O-H group

e.g. CH3 - CH(CH3) - CH2 - CH2 - CH(OH) - CH3 is called 5-

methylhexan-2-ol
 STRUCTURAL ISOMERISM IN
ALCOHOLS
Different structures are possible due to...

A Different positions for the OH group and

B Branching of the carbon chain
butan-1-ol butan-2-ol

2- 2-
methylpropan- methylpropan-
2-ol 1-ol
 BOILING POINTS OF ALCOHOLS

Increases with molecular size due to increased van der Waals’ forces.

Alcohols have higher boiling points than

similar molecular mass alkanes

This is due to the added presence of

inter-molecular hydrogen bonding.
More energy is required to separate the molecules.

Mr bp / °C
propane C3H8 44 -42 permanent dipole-dipole interactions
ethanol C2H5OH 46 +78 permanent forces + hydrogen
bonding
 BOILING POINTS OF ALCOHOLS

Increases with molecular size due to increased van der Waals’ forces.

Alcohols have higher boiling points than

similar molecular mass alkanes

This is due to the added presence of

inter-molecular hydrogen bonding.
More energy is required to separate the molecules.

Mr bp / °C
propane C3H8 44 -42 permanent dipole-dipole interactions
ethanol C2H5OH 46 +78 permanent forces + hydrogen bonding

Boiling point is higher for “straight” chain isomers.

bp / °C
Greater branching =
butan-1-ol CH3CH2CH2CH2OH 118
lower inter-molecular forces
butan-2-ol CH3CH2CH(OH)CH3 100
2-methylpropan-2-ol (CH3)3COH 83
 BOILING POINTS OF ALCOHOLS

Increases with molecular size due to increased van der Waals’ forces.

Alcohols have higher boiling points than

similar molecular mass alkanes

This is due to the added presence of

inter-molecular hydrogen bonding.
More energy is required to separate the molecules.

Mr bp / °C
propane C3H8 44 -42 just van der Waals’ forces
ethanol C2H5OH 46 +78 van der Waals’ forces + hydrogen bonding

Boiling point is higher for “straight” chain isomers.

bp / °C
butan-1-ol CH3CH2CH2CH2OH 118
Greater branching =
butan-2-ol CH3CH2CH(OH)CH3 100
lower inter-molecular forces
2-methylpropan-2-ol (CH3)3COH 83
 SOLVENT PROPERTIES OF ALCOHOLS

Solubility Low molecular mass alcohols are miscible with

water
Due to hydrogen bonding between the two molecules
Heavier alcohols are less miscible

Show the relevant lone pair(s) when drawing

Solvent hydrogen bonding
properties Alcohols are themselves very good solvents
They dissolve a large number of organic molecules
 CHEMICAL PROPERTIES OF ALCOHOLS

The OXYGEN ATOM HAS TWO LONE PAIRS; this makes alcohols...

BASES Lewis bases are lone pair donors

Bronsted-Lowry bases are proton acceptors

The alcohol uses one of its lone pairs to form a co-ordinate bond

NUCLEOPHILES Alcohols can use the lone pair to attack electron

deficient centres
 ELIMINATION OF WATER (DEHYDRATION)

Reagent/catalyst conc. sulphuric acid (H2SO4) or conc. phosphoric acid (H3PO4)

Conditions reflux at 180°C
Product alkene
Equation e.g. C2H5OH(l) ——> CH2 = CH2(g) + H2O(l)
Mechanism

Step 1 protonation of the alcohol using a lone pair on oxygen

Step 2 loss of a water molecule to generate a carbocation
Step 3 loss of a proton (H+) to give the alkene

Alternative
Method Pass vapour over a heated alumina (aluminium oxide) catalyst
 ELIMINATION OF WATER (DEHYDRATION)

MECHANISM

Step 1 protonation of the alcohol using a lone pair on oxygen

Step 2 loss of a water molecule to generate a carbocation
Step 3 loss of a proton (H+) to give the alkene

Note 1 There must be an H on a carbon atom adjacent the carbon with the OH

Note 2 Alcohols with the OH in the middle of a chain

can have two ways of losing water.

In Step 3 of the mechanism, a proton can be lost

from either side of the carbocation. This gives a
mixture of alkenes from unsymmetrical alcohols...
 OXIDATION OF ALCOHOLS

All alcohols can be oxidised depending on the conditions

Oxidation is used to differentiate between primary, secondary and tertiary alcohols

The usual reagent is acidified potassium dichromate(VI)

Primary Easily oxidised to aldehydes and then to carboxylic acids.

Secondary Easily oxidised to ketones

Tertiary Not oxidised under normal conditions.

They do break down with very vigorous oxidation

PRIMARY 1° SECONDARY 2°
TERTIARY 3°
 OXIDATION OF PRIMARY ALCOHOLS
Primary alcohols are easily oxidised to aldehydes

e.g. CH3CH2OH(l) + [O] ——> CH3CHO(l) + H2O(l)

ethanol ethanal

it is essential to distil off the aldehyde before it gets oxidised to the

acid

CH3CHO(l) + [O] ——> CH3COOH(l)

ethanal ethanoic acid
 OXIDATION OF PRIMARY ALCOHOLS
Primary alcohols are easily oxidised to aldehydes
e.g. CH3CH2OH(l) + [O] ——> CH3CHO(l) + H2O(l)
ethanol ethanal
it is essential to distil off the aldehyde before it gets oxidised to the acid

CH3CHO(l) + [O] ——> CH3COOH(l)

ethanal ethanoic acid
Practical details
• the alcohol is dripped into a warm solution of acidified K 2Cr2O7
• aldehydes have low boiling points - no hydrogen bonding - they distil off immediately
• if it didn’t distil off it would be oxidised to the equivalent carboxylic acid
• to oxidise an alcohol straight to the acid, reflux the mixture
compound formula intermolecular bonding boiling point
ETHANOL C2H5OH HYDROGEN BONDING 78°C
ETHANAL CH3CHO DIPOLE-DIPOLE 23°C
ETHANOIC ACID CH3COOH HYDROGEN BONDING 118°C
 OXIDATION OF PRIMARY ALCOHOLS

Controlling the products

e.g. CH3CH2OH(l) + [O] ——> CH3CHO(l) + H2O(l)

then CH3CHO(l) + [O] ——> CH3COOH(l)

OXIDATION TO OXIDATION TO CARBOXYLIC

ALDEHYDES ACIDS
DISTILLATION REFLUX

Aldehyde has a lower boiling point so Aldehyde condenses back into the
distils off before being oxidised mixture and gets oxidised to the
further acid
 OXIDATION OF SECONDARY ALCOHOLS
Secondary alcohols are easily oxidised to ketones

e.g. CH3CHOHCH3(l) + [O] ——> CH3COCH3(l)

+ H2O(l)
propan-2-ol propanone

The alcohol is refluxed with acidified K2Cr2O7. However, on

prolonged treatment with a powerful oxidising agent they can be
further oxidised to a mixture of acids with fewer carbon atoms than
the original alcohol.
 OXIDATION OF SECONDARY ALCOHOLS
Secondary alcohols are easily oxidised to ketones

e.g. CH3CHOHCH3(l) + [O] ——> CH3COCH3(l) +

H2O(l)
propan-2-ol propanone

The alcohol is refluxed with acidified K2Cr2O7. However, on prolonged

treatment with a powerful oxidising agent they can be further oxidised to
a mixture of acids with fewer carbon atoms than the original alcohol.

OXIDATION OF TERTIARY ALCOHOLS

Tertiary alcohols are resistant to normal oxidation
 OXIDATION OF ALCOHOLS
Why 1° and 2° alcohols are easily oxidised and 3° alcohols are not

For oxidation to take place easily you must have two hydrogen atoms on
adjacent C and O atoms.
 OXIDATION OF ALCOHOLS
Why 1° and 2° alcohols are easily oxidised and 3° alcohols are not

For oxidation to take place easily you must have two hydrogen atoms on
adjacent C and O atoms.

H H
1° R C O + [O] R C O + H 2O
H H
 OXIDATION OF ALCOHOLS
Why 1° and 2° alcohols are easily oxidised and 3° alcohols are not

For oxidation to take place easily you must have two hydrogen atoms on
adjacent C and O atoms.

H H
1° R C O + [O] R C O + H 2O
H H
H H
2° R C O + [O] R C O + H 2O
R R
 OXIDATION OF ALCOHOLS
Why 1° and 2° alcohols are easily oxidised and 3° alcohols are not

For oxidation to take place easily you must have two hydrogen atoms on
adjacent C and O atoms.

H H
1° R C O + [O] R C O + H 2O
H H
H H
2° R C O + [O] R C O + H 2O
R R

This is possible in 1° and 2° alcohols but not in 3° alcohols.

 OXIDATION OF ALCOHOLS
Why 1° and 2° alcohols are easily oxidised and 3° alcohols are not

For oxidation to take place easily you must have two hydrogen atoms on
adjacent C and O atoms.
H H
1° R C O + [O] R C O + H2 O
H H
H H
2° R C O + [O] R C O + H2 O
R R

This is possible in 1° and 2° alcohols but not in 3° alcohols.

R H
3° R C O + [O]
R
 ESTERIFICATION OF ALCOHOLS
Reagent(s) carboxylic acid + strong acid catalyst (e.g conc. H2SO4 )
Conditions reflux
Product ester
Equation e.g. CH3CH2OH(l) + CH3COOH(l) CH3COOC2H5(l) +
H2O(l)
ethanol ethanoic acid ethyl ethanoate

Notes Concentrated H2SO4 is a dehydrating agent - it removes water

causing the equilibrium to move to the right and increases the yield
 ESTERIFICATION OF ALCOHOLS
Reagent(s) carboxylic acid + strong acid catalyst (e.g conc. H 2SO4 )
Conditions reflux
Product ester
Equation e.g. CH3CH2OH(l) + CH3COOH(l) CH3COOC2H5(l) + H2O(l)
ethanol ethanoic acid ethyl ethanoate
Notes Concentrated H2SO4 is a dehydrating agent - it removes water
causing the equilibrium to move to the right and increases the yield
Uses of esters Esters are fairly unreactive but that doesn’t make them useless
Used as flavourings

Naming esters Named from the alcohol and carboxylic acid which made them...

CH3OH + CH3COOH CH3COOCH3 + H2O

from ethanoic acid CH3COOCH3 from methanol

METHYL ETHANOATE
 OTHER REACTIONS OF ALCOHOLS
OXYGEN Alcohols make useful fuels
C2H5OH(l) + 3O2(g) ———> 2CO2(g) + 3H2O(l)

Advantages have high enthalpies of combustion

do not contain sulphur so there is less pollution
can be obtained from renewable resources
 OTHER REACTIONS OF ALCOHOLS
OXYGEN Alcohols make useful fuels
C2H5OH(l) + 3O2(g) ———> 2CO2(g) + 3H2O(l)

Advantages have high enthalpies of combustion

do not contain sulphur so there is less pollution
can be obtained from renewable resources
SODIUM
Conditions room temperature
Product sodium alkoxide and hydrogen
Equation 2CH3CH2OH(l) + 2Na(s) ——> 2CH3CH2O¯ Na + + H2(g)
sodium ethoxide
Notes alcohols are organic chemistry’s equivalent of water
water reacts with sodium to produce hydrogen and so do alcohols
the reaction is slower with alcohols than with water.

Alkoxides are white, ionic crystalline solids e.g. CH3CH2O¯ Na+

 BROMINATION OF ALCOHOLS

Reagent(s) conc. hydrobromic acid HBr(aq) or

sodium (or potassium) bromide and concentrated sulphuric acid
Conditions reflux
Product haloalkane
Equation C2H5OH(l) + conc. HBr(aq) ———> C 2H5Br(l) +
H2O(l)

Mechanism The mechanism starts off similar to that involving dehydration

(protonation of the alcohol and loss of water) but the carbocation
(carbonium ion) is attacked by a nucleophilic bromide ion in step 3

Step 1 protonation of the alcohol using a lone pair on oxygen

Step 2 loss of a water molecule to generate a carbocation (carbonium ion)
Step 3 a bromide ion behaves as a nucleophile and attacks the carbocation
 INFRA-RED SPECTROSCOPY

Chemical bonds vibrate at different frequencies. When infra red (IR) radiation is passed through a
liquid sample of an organic molecule, some frequencies are absorbed. These correspond to the
frequencies of the vibrating bonds.

Most spectra are very complex due to the large number of bonds present and each molecule
produces a unique spectrum. However, the presence of certain absorptions can be used to identify
functional groups.

BOND COMPOUND ABSORBANCE RANGE

O-H alcohols broad 3200 cm-1 to 3600 cm-1

O-H carboxylic acids medium to broad 2500 cm-1 to 3500 cm-1

C=O ketones, aldehydes strong and sharp 1600 cm-1 to 1750 cm-1
esters and acids
 INFRA-RED SPECTROSCOPY
IDENTIFYING ALCOHOLS USING INFRA RED SPECTROSCOPY

Differentiation Compound O-H C=O

ALCOHOL YES NO
ALDEHYDE / KETONE NO YES
CARBOXYLIC ACID YES YES
ESTER NO YES

ALCOHOL ALDEHYDE CARBOXYLIC ACID

PROPAN-1-OL PROPANAL PROPANOIC ACID

O-H absorption C=O absorption O-H + C=O absorption

 INDUSTRIAL PREPARATION OF
ALCOHOLS

FERMENTATION

Reagent(s) GLUCOSE - produced by the hydrolysis of starch

Conditions yeast
warm, but no higher than 37°C

Equation C6H12O6 ——> 2 C2H5OH + 2 CO2

 INDUSTRIAL PREPARATION OF ALCOHOLS
FERMENTATION

Reagent(s) GLUCOSE - produced by the hydrolysis of starch

Conditions yeast
warm, but no higher than 37°C

Equation C6H12O6 ——> 2 C2H5OH + 2 CO2

Advantages LOW ENERGY PROCESS

USES RENEWABLE RESOURCES - PLANT MATERIAL
SIMPLE EQUIPMENT

Disadvantages SLOW
PRODUCES IMPURE ETHANOL
BATCH PROCESS
 INDUSTRIAL PREPARATION OF
ALCOHOLS

HYDRATION OF ETHENE

Reagent(s) ETHENE - from cracking of fractions from

distilled crude oil

Conditions catalyst - phosphoric acid

high temperature and pressure

Equation C2H4 + H2O ——> C2H5OH

 INDUSTRIAL PREPARATION OF
ALCOHOLS
HYDRATION OF ETHENE
Reagent(s) ETHENE - from cracking of fractions from distilled crude oil
Conditions catalyst - phosphoric acid
high temperature and pressure
Equation C2H4 + H2O ——> C2H5OH

Advantages FAST
PURE ETHANOL PRODUCED
CONTINUOUS PROCESS

Disadvantages HIGH ENERGY PROCESS

EXPENSIVE PLANT REQUIRED
USES NON-RENEWABLE FOSSIL FUELS TO MAKE ETHENE

Uses of ethanol ALCOHOLIC DRINKS

SOLVENT - industrial alcohol / methylated spirits
FUEL - petrol substitute in countries with limited oil reserves
 USES OF ALCOHOLS
ETHANOL
DRINKS
SOLVENT industrial alcohol / methylated spirits (methanol is added)
FUEL used as a petrol substitute in countries with limited oil
reserves

METHANOL
PETROL ADDITIVE improves combustion properties of unleaded petrol
SOLVENT
RAW MATERIAL used as a feedstock for important industrial
processes
FUEL

Health warning Methanol is highly toxic

ALCOHOL
II
Physical properties of alcohols
Alcohols are noticeably less volatile; their melting points are
greater and they are more water soluble than the corresponding
hydrocarbons having similar molecular weights.

These differences are due to the OH group which renders a

certain polarity to the molecule. The result is an important
intermolecular attraction:
- + - + -
O H O H O H
R R R

the hydrogen bond

~ 21 - 25 kJ/mol
Solubility of Alcohols
Low molecular weight alcohols are water
soluble:
- + - + - +
O H O H O H
R H R
Fermentation

Fermentation of sugar by yeast gives C2H5OH.

Methanol is added to denature it.
Oxymercuration

1. Hg(OAc)2, H2O/THF
CH3
CH3
2. NaBH4 OH
 Oxymercuration
An anti addition via a mercurinium ion:

-
+
Dissociation: Hg(OAc)2 CH3CO2 + HgOCOCH3
+
HgOCOCH3
Electrophilic +
CH3 HgOCOCH3 CH3
attack:

+
HgOCOCH3 CH3
Nucleophilic OH
opening: CH3 HgOCOCH3
H
H-O-H
 Oxymercuration
Why do we observe Markovnikov addition?

+ 
HgOAc
HgOAc


In the mercurinium ion, the positive charge is shared between

the more substituted carbon and the mercury atom.
Only a small portion of the charge resides on this carbon but it
is sufficient to account for the orientation of the addition but is
insufficient to allow a rearrangement to occur.
Hydroboration

H2O2
+ (BH3)2 + B(OH)3
-
H B OH H OH
diborane
Hydroboration
1. (BH3)2 3HC H
syn
addition
H 3C 2. H2O2/OH- H OH
trans-2-methyl-
cyclopentanol

(CH3)3CCH=CH2 (CH3)3CCH2CH2OH

no rearrangement
no carbocation!
Mechanism

1. (BH3)2
CH3CH=CH2 - CH3CH2CH2OH
2. H2O2/OH


HX +
CH3CH=CH2 CH3CH CH2 CH3CHCH3 + X-

X 
Hydroboration - the mechanism
1. (BH3)2
CH3CH=CH2 - CH3CH2CH2OH
2. H2O2/OH


CH3 > CH CH2

H B H
H

CH3 > CH CH2

H B H
H
Hydroboration - the mechanism
R R
-
R B O-OH R -B O OH
R R
R R
R -B O OH B OR + HO-

R R
RO HO-
B OR 3ROH + BO33-
RO
Reduction of carbonyls
H2 + Ni, Pt or Pd

O H
C
O
LiAlH 4 or NaBH4 H
followed by H+
Reduction of carbonyls
LiAlH H+ H
4
O
OH

H 2 /Ni
CH CH=CHCHO CH CH CH CH OH
3 3 2 2 2

CH=CHCHO NaBH H+ CH=CHCH 2OH

4

cinnamaldehyde
Reduction of carbonyls
-
H 3B H O H O-

-
H 2O
H O H OH

hydride transfer
Reduction of acids
1. LiAlH4, THF
RCO2H + RCH2OH
2. H3O
1o alcohol
 Reduction of esters
i. LiAlH 4
O
+
RCH 2OH + R'OH
R OR' ii. H

O
1. LiAlH4
CH3CH2CH=CHCOCH2CH3
2. H+

CH3CH2CH=CHCH2OH + CH3CH2OH
Reactivity of the carbonyl group


R
o  
120 C O
'R

2
sp
Nucleophilic addition
 +
R :Nu Nu  Nu
O R O -
R O
'R R' R'

+ +
Nu H 2O Nu
-
R O R OH
R' R'
Preparation of alcohols - Grignard
synthesis
dry
RX + Mg RMgX
ether
  - +
R MgX O R O MgX

- + H2O
R O MgX R OH + Mg(OH)X
Grignard synthesis
H RMgX H H3O+ H
C O H C OMgX H OH
H R R
formaldehyde primary alcohol

' '
R RMgX R H3O+ 'R
C O H C OMgX H OH
H R R
aldehyde secondary alcohol
Grignard synthesis
' '
R RMgX R
''
H3O+ 'R
C O R C OMgX "R OH
''
R R R
ketone tertiary alcohol

H O H RMgX H3O+
RCH2CH2OMgX RCH2CH2OH
H H

ethylene oxide primary alcohol

Planning a Grignard synthesis

CH3
H3CH2CH2CH2C C OH
Reactions of alcohols
The reactions of alcohols involve one of two processes:

• breaking of the O-H bond

• breaking of the C-O bond
Reactions involving O-H bond breaking

R-OH + M RO- + M+ + 1/2 H2

Na
CH3CH2OH CH3CH2O- Na+
sodium ethoxide
Phenols
OH-
-
ArOH ArO
water H+ phenoxide ion
insoluble soluble

Ka ~ 10-10
Acidity of phenols

ArOH + H 2O ArO - + H 3O +
Acidity
ROH H+ + RO -
OH OH + OH + OH + OH
- -

O- O- O O O
- -

-
Substituent effects

OH O

+ H+
-

G G
An electron attracting substituent stabilizes the conjugate base. The equilibrium is
shifted to the right.
Substituent effects

OH O

- + H+

G G

Electron donating substituents reduce the acidity of phenols.

Substituent effects
OH OH OH

CH3 NO2
 Reaction with hydrogen halides
ROH + HX RX + H2O

HX: HI > HBr > HCl

ROH: allyl > 3o > 2o > 1o < CH3OH

HBr or
CH3CHCH3 CH3CHCH3
OH NaBr/H2SO4 Br
Experimental facts
1. The reaction is acid catalyzed

2. Rearrangements are possible

CH 3 H HCl CH 3 H
H3C C C CH 3 H3C C C CH 3
H OH Cl H

3. Alcohol reactivity is 3o > 2o > 1o < CH3OH

The mechanism
H+
C C C C
H OH H OH2
+

C C C C + H2O
H OH2 H +
+

C C C C
H + H X
-
X
SN 1
Reaction of primary alcohols with HX
+ -
1. ROH + HX ROH2 + X
1o

+ - +
2. ROH2 + X- X R OH2 RX + H2O

SN2

HX: HI > HBr > HCl

This reflects nucleophile strength in a protic solvent.

 Reactions with phosphorus halides
and with thionyl chloride

ROH + PX3 RX + H3PO3

O
SOCl2 SN2
RCH2OH RCH2-O-S-Cl RCH2Cl + SO2 + HCl
-
Cl

Creates a good leaving group from 1o and 2o alcohols.

Tosylates
O -
CH3CH2OH + Cl S CH3 H +O
O S CH3
O H3CH2C O Cl
p-toluenesulfonyl
chloride
B: H O
+
O S CH3
H3CH2C O O
H3CH2CO S CH3
O
ethyl p-toluenesulfonate
a tosylate
Why form tosylates?
Sulfonate ions are excellent leaving groups:

O
Nu: C O S CH3
O
O
-
Nu C O S CH3
O
Dehydration
H H3PO4
C C + H2O
OH 

OH H3PO4/
Dehydration
H+
C C C C
H OH H OH2
+

C C C C + H2O
H OH2 H +
+

C C C C
H +
B:
E1 mechanism
Oxidation of primary alcohols
C5H5NHCrO3Cl O C5H5NHCrO3Cl -
RCH2OH pyridinium
or K2Cr2O7 R H chlorochromate in
CH2Cl2 - PCC
KMnO4
KMnO4
or
K2Cr2O7

O
R OH

C5H5NHCrO3Cl
CH3CH2CH2OH CH3CH2C=O
CH2Cl2
H
Oxidation of secondary alcohols
+ -
C5H5NH CrO3Cl, O
R2CHOH
K2Cr2O7, R R
CrO3, or
KMnO4
R

CrO3
HOAc O
HO
3-cholestanol 3-cholestanone
Synthesis of alcohols
SOCl2 Mg
alcohol alkyl halide Grignard reagent

PCC
alcohol
aldehyde
or ketone

CH3CH2OH CH3CHOHCH2CH3
THANKS FOR LISTERNING
Synthesis of alcohols
CH3CH2OH CH3CHOHCH2CH3
SOCl2 Mg
CH3CH2OH CH3CH2Cl CH3CH2MgCl

PCC O
CH3CH2OH H3CC
H
O 1. CH3CH2MgCl
H3CC CH3CHOHCH2CH3
+
H 2. H3O