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Reactions of Alcohols
Susan F. Hornbuckle
Associate Professor of Chemistry
Clayton State University
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Reaction= s Flow Chart
3D"Organization
What are the
reaction condition= s?
H2<= /span>SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2<= /span>SO4 / 14= 0o<= /span>C
“= ;Intra or Intermolecular
Dehydration”=
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2<= /span>Cr2O7 = / H2SO4&= #13;
“= ;Oxidation Conditions”
 =
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.
2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
1o<= /span>
=
Redraw= the alcohol.
Remove the
hydroxyl group = 3;
from one and the &= #13;
hydrox= yl-hydrogen
from the other to =
form an ETHER
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
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3D"Organization
What are the
reaction
conditions?
H2SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2SO4 / 140oC
“= ;Intra or Intermolecular
Dehydration”=
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2Cr2O7 / H<= /b>2SO4
“= ;Oxidation Conditions”
 =
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.

2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
<= /span>
1o<= /span>
=
Redraw= the alcohol. 
Remove the
hydroxyl group = 3;
from one and the &= #13;
hydroxy= l-hydrogen
from the other to =
form an ETHER. = ;
.
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
=
Ex= ample 1
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3D"Organization
What are the
reaction
conditions?
H2SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2SO4 / 140oC
“= ;Intra or Intermolecular
Dehydration”=
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2Cr2O7 / H<= /b>2SO4
“= ;Oxidation Conditions”
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.
=
2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
=
1o<= /span>
=
Redraw= the alcohol. 
Remove the
hydroxyl group = 3;
from one and the &= #13;
hydroxy= l-hydrogen
from the other to =
form an ETHER. = ;
.
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
Ex= ample 1
=
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3D"Organization
What are the
reaction
conditions?
H2SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2SO4 / 140oC
“= ;Intra or Intermolecular
Dehydration”=
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2Cr2O7 / H<= /b>2SO4
“= ;Oxidation Conditions”
 =
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.
=
2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
=
1o<= /span>
=
Redraw= the alcohol.
Remove the
hydroxyl group = 3;
from one and the &= #13;
hydrox= yl-hydrogen
from the other to =
form an ETHER. = ;
.
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
Ex= ample 1
=
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charset="us-ascii" Slide 1
3D"Organization
What are the
reaction
conditions?
H2SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2SO4 / 140oC
“= ;Intra or Intermolecular
Dehydration”=
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2Cr2O7 / H<= /b>2SO4
“= ;Oxidation Conditions”
 =
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.
=
2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
=
1o<= /span>
=
Redraw= the alcohol. 
Remove the
hydroxyl group = 3;
from one and the &= #13;
hydrox= yl-hydrogen
from the other to =
form an ETHER. = ;
.
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
Ex= ample 1
=
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3D"Organization
What are the
reaction
conditions?
H2SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2SO4 / 140oC
“= ;Intra or Intermolecular
Dehydration”=
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2Cr2O7 / H<= /b>2SO4
“= ;Oxidation Conditions”
 =
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.
2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
=
1o<= /span>
=
Redraw the alcohol= .
Remove the
hydroxyl group = 3;
from one and the &= #13;
hydroxy= l-hydrogen
from the other to =
form an ETHER. = ;
.
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
Ex= ample 2
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3D"Organization
What are the
reaction
conditions?
H2SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2SO4 / 140oC
“= ;Intra or Intermolecular
Dehydration”=
Is the starting
alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2Cr2O7 / H<= /b>2SO4
“= ;Oxidation Conditions”
 =
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.
=
2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
=
1o<= /span>
=
Redraw= the alcohol.
 Remove the
hydroxyl group = 3;
from one and the &= #13;
hydrox= yl-hydrogen
from the other to =
form an ETHER..
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
Ex= ample 2
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3D"Organization
What are the
reaction
conditions?
H2SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2SO4 / 140oC
“= ;Intra or Intermolecular
Dehydration”=
Is the starting
alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2Cr2O7 / H<= /b>2SO4
“= ;Oxidation Conditions”
 =
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.
=
2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
=
1o<= /span>
=
Redraw= the alcohol.
Remove the
hydroxyl group = 3;
from one and the &= #13;
hydroxy= l-hydrogen
from the other to =
form an ETHER. = ;
.
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
Ex= ample 2
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file:///C:/CD25C9F3/CHEM1152ReactionsofAlcohols_files/slide0014.htm Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset="us-ascii" Slide 1
3D"Organization
What are the
reaction
conditions?
H2SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2SO4 / 140oC
“= ;Intra or Intermolecular
Dehydration”=
Is the starting
alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2Cr2O7 / H<= /b>2SO4
“= ;Oxidation Conditions”
 =
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.

2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
=
1o<= /span>
=
Redraw= the alcohol.
Remove the
hydroxyl group = 3;
from one and the &= #13;
hydrox= yl-hydrogen
from the other to =
form an ETHER. = ;
.
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
Ex= ample 2
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3D"Organization
What are the
reaction
conditions?
H2SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2SO4 / 140oC
“= ;Intra or Intermolecular
Dehydration”=
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2Cr2O7 / H<= /b>2SO4
“= ;Oxidation Conditions”
 =
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.

2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
=
1o<= /span>
=
Redraw= the alcohol.
Remove the
hydroxyl group = 3;
from one and the &= #13;
hydrox= yl-hydrogen
from the other to =
form an ETHER. = ;
.
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
Ex= ample 3
=
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3D"Organization
What are the
reaction
conditions?
H2SO4 / 180oC
=
“I= ntramolecular
Dehydration”
H2SO4 / 140oC
“= ;Intra or Intermolecular
Dehydration”=
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
K2Cr2O7 / H<= /b>2SO4
“= ;Oxidation Conditions”
 =
Is the starting alcohol
1o<= /span>, 2o, or = 3o<= /span>?
1o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen to
 form an ALDEHYDE.
2o<= /span>  = ;
Remove= the alpha-
hydrogen and the <= br> hydroxyl-hydrogen = to
form a KETONE.
3o&= #13;
NO RXN.

2o<= /span>  or<= span style=3D'mso-spacerun:yes'>  3o
=
1o<= /span>
=
Redraw= the alcohol.
Remove the
hydroxyl group = 3;
from one and the &= #13;
hydrox= yl-hydrogen
from the other to =
form an ETHER. = ;
.
Remove t= he
hydroxyl group and
the beta-hydrogen to
form an ALKENE. 
Rem. Zaitzef’s Rule.
Insert an oxygen
atom in the C-H bond of  the carbonyl
to form  a
CARBOXYLIC ACID.
Ex= ample 3
=
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