Alcohols are very useful organic compounds because there are many ways to synthesize larger and more complex molecules starting with simple alcohols. The reactions you will examine form a strong basis for synthetic tools that an organic chemist would use. You will be expected to predict the major products of reactions under the conditions given. The key to doing this is to look carefully at the conditions and remember how those conditions affect the products. It is a good idea to have an index card file of the reactions as you learn them. Dehydration (loss of water) - There are two forms of dehydration reactions with alcohols - ether formation and elimination (alkene formation). In both reactions you are looking for the components of water (OH and H) that will be removed in the reaction. Ether Formation - Two alcohols will form an ether link by loss of water forming an ether product with an acidic catalyst (typically H2SO4) at 140\deg C. One alcohol loses the hydroxyl group and one loses the H from its hydroxyl group. There are ways of predicting which will lose which, but that is not important now. Ethers can be formed from two molecules of the same alcohol or two different alcohols. When you have two different alcohols you usually get a mixture of the possible ethers. How many possibilities would there be ?

Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter20: Acidity And Pka Of Phenols
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Alcohols are very useful organic compounds because there are many ways to synthesize larger and more
complex molecules starting with simple alcohols. The reactions you will examine form a strong basis for
synthetic tools that an organic chemist would use. You will be expected to predict the major products of
reactions under the conditions given. The key to doing this is to look carefully at the conditions and
remember how those conditions affect the products. It is a good idea to have an index card file of the
reactions as you learn them. Dehydration (loss of water) - There are two forms of dehydration reactions
with alcohols - ether formation and elimination (alkene formation). In both reactions you are looking for
the components of water (OH and H) that will be removed in the reaction. Ether Formation - Two alcohols
will form an ether link by loss of water forming an ether product with an acidic catalyst (typically H2SO4) at
140\deg C. One alcohol loses the hydroxyl group and one loses the H from its hydroxyl group. There are
ways of predicting which will lose which, but that is not important now. Ethers can be formed from two
molecules of the same alcohol or two different alcohols. When you have two different alcohols you usually
get a mixture of the possible ethers. How many possibilities would there be ?
Transcribed Image Text:Alcohols are very useful organic compounds because there are many ways to synthesize larger and more complex molecules starting with simple alcohols. The reactions you will examine form a strong basis for synthetic tools that an organic chemist would use. You will be expected to predict the major products of reactions under the conditions given. The key to doing this is to look carefully at the conditions and remember how those conditions affect the products. It is a good idea to have an index card file of the reactions as you learn them. Dehydration (loss of water) - There are two forms of dehydration reactions with alcohols - ether formation and elimination (alkene formation). In both reactions you are looking for the components of water (OH and H) that will be removed in the reaction. Ether Formation - Two alcohols will form an ether link by loss of water forming an ether product with an acidic catalyst (typically H2SO4) at 140\deg C. One alcohol loses the hydroxyl group and one loses the H from its hydroxyl group. There are ways of predicting which will lose which, but that is not important now. Ethers can be formed from two molecules of the same alcohol or two different alcohols. When you have two different alcohols you usually get a mixture of the possible ethers. How many possibilities would there be ?
Alcohol Reactions
Alcohols are very useful organic compounds because there are many ways to synthesize
larger and more complex molecules starting with simple alcohols. The reactions you will
examine form a strong basis for synthetic tools that an organic chemist would use. You
will be expected to predict the major products of reactions under the conditions given.
The key to doing this is to look carefully at the conditions and remember how those
conditions affect the products. It is a good idea to have an index card file of the reactions
as you leam them.
Dehydration (less of water) - There are two fams of dehydration reactions with
alcohols-ether formation and elimination (alkene formation). In both reactions you are
looking for the components of water (OH and H) that will be removed in the reaction.
Ether Formation - Two alcohols will form an ether link by loss of water forming an ether
product with an acidic catalyst (typically H,SO,) at 140°C.
HQ HH
Hyso
140 C
++++
11,0
One alcohol loses the hydroxyl group and one loses the H from its hydroxyl group.
There are ways of predicting which will lose which, but that is not important now. Ethers
can be formed from two molecules of the same alcohol or two different alcohols. When
you have two different alcohols you usually get a mixture of the possible ethers. How
mans possibilities would there be?
Alcohol Reactions, p. 2 of 4
Predict the major product from the reactants below (neglect any mixtures of products for
now).
H
4
H
H
H
1199
AAAA
A
AH
H H
H
H
Elimination - Alkenes can be formed by the internal loss of a water molecule from an
alcohol. To predict the product you must have a hydrogen atom available on a carbon
next to the carbon with the hyroxy group. A double bond then forms from the carbon that
loses the hydroxyl group and the carbon that loses the hydrogen. Again, the reaction
takes place with an acid catalyst, but this time at 180°C.
H₂SO,
180 C
Predict the product from the following conditions.
HSO4
|
H H H
180 C
H
H
H
H
H
H₂SO4
H H
140 C
+HO
A complication arises when you have more than one hydrogen to remove to form the
alkene. Then we follow SaytrefCs rule:
Translated into English, this means that the alkene with the most carbons attached to the
double-bonded carbons is the favored product.
telo
H,SO,
180 C
Alcohol Reactions, p. 3 of 4
H₂SO,
180 C
+ HO
DA
Notice that there are several possible bydgens for removal in the molecule. We are
only interested in one per carbon because the others are the same. If we remove the
circled hydrogen labeled A, we get the top alkene (2-butene) with 2 methyl groups. If we
remove the circled hydrogen labeled B, we get the bottom alkene (1-butene) with an ethyl
group. The top alkene is favored because it has 2 alkyl groups attached to the double-
bonded carbons and the other choice caly has one.
+HO
Predict the major product under these conditions.
H-C C
A)
H
B)
H H
30-
-C
H
CH, H
Predict the products of the following reactions:
H-
H
H
H H H H
H
C-C-H
CH₁ H
H-904
180 C
C) (harder, but you can do it!)
CH;
H
OH
&
H
H
H-804
Alcohol Reactions, p. 4 of 4
180 C
H₂SO4
H₂SO4
+=
140 C
180 C
Transcribed Image Text:Alcohol Reactions Alcohols are very useful organic compounds because there are many ways to synthesize larger and more complex molecules starting with simple alcohols. The reactions you will examine form a strong basis for synthetic tools that an organic chemist would use. You will be expected to predict the major products of reactions under the conditions given. The key to doing this is to look carefully at the conditions and remember how those conditions affect the products. It is a good idea to have an index card file of the reactions as you leam them. Dehydration (less of water) - There are two fams of dehydration reactions with alcohols-ether formation and elimination (alkene formation). In both reactions you are looking for the components of water (OH and H) that will be removed in the reaction. Ether Formation - Two alcohols will form an ether link by loss of water forming an ether product with an acidic catalyst (typically H,SO,) at 140°C. HQ HH Hyso 140 C ++++ 11,0 One alcohol loses the hydroxyl group and one loses the H from its hydroxyl group. There are ways of predicting which will lose which, but that is not important now. Ethers can be formed from two molecules of the same alcohol or two different alcohols. When you have two different alcohols you usually get a mixture of the possible ethers. How mans possibilities would there be? Alcohol Reactions, p. 2 of 4 Predict the major product from the reactants below (neglect any mixtures of products for now). H 4 H H H 1199 AAAA A AH H H H H Elimination - Alkenes can be formed by the internal loss of a water molecule from an alcohol. To predict the product you must have a hydrogen atom available on a carbon next to the carbon with the hyroxy group. A double bond then forms from the carbon that loses the hydroxyl group and the carbon that loses the hydrogen. Again, the reaction takes place with an acid catalyst, but this time at 180°C. H₂SO, 180 C Predict the product from the following conditions. HSO4 | H H H 180 C H H H H H H₂SO4 H H 140 C +HO A complication arises when you have more than one hydrogen to remove to form the alkene. Then we follow SaytrefCs rule: Translated into English, this means that the alkene with the most carbons attached to the double-bonded carbons is the favored product. telo H,SO, 180 C Alcohol Reactions, p. 3 of 4 H₂SO, 180 C + HO DA Notice that there are several possible bydgens for removal in the molecule. We are only interested in one per carbon because the others are the same. If we remove the circled hydrogen labeled A, we get the top alkene (2-butene) with 2 methyl groups. If we remove the circled hydrogen labeled B, we get the bottom alkene (1-butene) with an ethyl group. The top alkene is favored because it has 2 alkyl groups attached to the double- bonded carbons and the other choice caly has one. +HO Predict the major product under these conditions. H-C C A) H B) H H 30- -C H CH, H Predict the products of the following reactions: H- H H H H H H H C-C-H CH₁ H H-904 180 C C) (harder, but you can do it!) CH; H OH & H H H-804 Alcohol Reactions, p. 4 of 4 180 C H₂SO4 H₂SO4 += 140 C 180 C
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