Page < > of 4 Alcohol Reactions Alcohols are very useful organic compounds because there are many ways to synthesize lar

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Page < > of 4 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 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°C. H₂SO4 4 H6 H=1116 H₂O 140 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?
2 Page < Alcohol Reactions, p. 2 of 4 Predict the major product from the reactants below (neglect any mixtures of products for now). HHHH H H H₂SO4 ++ + HO-C C C -H 140 C H H HH Answer 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. H To of 4 C
Page 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. H H (OHXH H H₂SO4 -H that H 180 C H H H Predict the product from the following conditions. H HOH H₂SO4 180 C +H₂O D
Page < Alcohol Reactions, p. 3 of 4 Answer: A complication arises when you have more than one hydrogen to remove to form the alkene. Then we follow Saytzeff's rule: Saytzeff's Rule: In elimination reactions, the most highly substituted alkene usually predominates. Translated into English, this means that the alkene with the most carbons attached to the double-bonded carbons is the favored product. B 1900 00 H₂SO4 -H 180 C H₂SO4 180 C H H (D- H- -H HH H H + H₂O + H₂O of 4 10
Page < Translated into English, this means that the alkene with the most carbons attached to the double-bonded carbons is the favored product. +y=00 H₂SO4 H 180 C H H₂SO4 180 C DIT +H₂O H H H Notice that there are several possible hydrogens 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 only has one. + H₂O of 4 | ZO
Predict the major product under these conditions. H HHH OHH H H CH3 H Answer: Predict the products of the following reactions: A) H H H H₂SO4 10 H 180 C H CHỊ H H B) HHOH H-C- H H -H H H₂SO4 180 C
Predict the products of the following reactions: A) H HOH H2SO4 Н --- 180 C HCH, H B) HHO •H Н C) (harder, but you can do it!) CH₂ H H OH -H H 'H H по-н Н- O-H H₂SO4 180 C H2SO4 140 C