Lecture 3 - Alcohols and Ethers

Lecture 3 - Alcohols and Ethers - BME 201 Suggested...

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1 BME 201 Suggested problems review material: Vollhardt & Shore, 6 th Ed., Chapter 6, problems no. 31-34, 38; Chapter 7, problem no.25; Chapter 8, problems 24-26 and exercises 8-15 and 8- 16; Chapter 9, problems 31, 41 Todays lecture is based on Vollhardt, selected material from chapters 6 and 7 ( haloalkanes ), chapter 8 ( alcohols ), chapter 9 ( ethers and thiols ) and selected handouts. Handouts may have marked chapter numbers and page numbers. You will find it easier to do the suggested problems and pass future quizzes and exams if you go over the reading prior to attempting to solve the suggested problems.
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2 Properties and Reactions of Haloalkanes
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3 Physical Properties of Haloalkanes 6-1 The bond strength of C-X decreases as the size of X increases.
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4 The C-X bond is polarized Because halogens are more electronegative that carbon, carbon- halogen bonds are polarized.
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5 Haloalkanes have higher boiling points than the corresponding alkanes. Boiling points of haloalkanes are higher than those of the parent alkanes mainly due to dipole-dipole interactions between the molecules: As the size of the halogen increases there are also larger London forces between the haloalkane molecules.
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6 Nucleophilic Substitution 6-2 Haloalkanes can react with nucleophiles at their electrophilic carbon atom. The nucleophile can be charged, as in :OH - or neutral, as in :NH 3 In nucleophilic substitution of haloalkanes, the nucleophile replaces the halogen atom. What was a nucleophile? Pages 218 ff
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7 Nucleophilic Substitution 6-2 Nucleophiles attack electrophillic centers.
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8 Nucleophililc substitution exhibits considerable diversity.
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9 Reaction Mechanisms Involving Polar Functional Groups: Using “Electron-Pushing” Arrows 6-3 Curved arrows depict the movement of electrons. The oxygen lone pair of electrons ends up being shared between the oxygen and the hydrogen. The bonding pair electrons in the HCl molecule ends up as a lone pair on the chloride ion. Pages 221 ff
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10 Nucleophilic Substitution Mechanism: Kinetics 6-4 Consider the reaction between chloromethane and sodium hydroxide: By measuring the rate product formation beginning with several different sets of reactant concentrations, a rate equation or rate law can be determined.
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11 Nucleophilic Substitution Mechanism: Kinetics 6-4 The reaction of chloromethane with sodium hydroxide is bimolecular ( Bimolecular nucleophilic substitution reactions are abbreviated SN2 ) The rate of a reaction can be measured by observing the appearance of one of the products, or by the disappearance of one of the reactants. These observations are consistent with a second-order process whose rate law is: Rate = k[CH 3 Cl][HO - ] mol L -1 s -1 .
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12 Hydroxy Functional Groups: Alcohols
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13 Alcohols can be thought of as a derivative of water in which a hydrogen atom has been replaced by an alkyl group.
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This note was uploaded on 02/20/2012 for the course BME 201 taught by Professor Schmidt during the Fall '11 term at Purdue University-West Lafayette.

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Lecture 3 - Alcohols and Ethers - BME 201 Suggested...

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