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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 ?

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 ?

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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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