Lecture19CHM233(10)final

Lecture19CHM233(10)final - Organic Chemistry, Third Edition...

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1 Organic Chemistry, Third Edition Janice Gorzynski Smith University of Hawai’i Chapter 7 Alkyl Halides and Nucleophilic Substitution
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How many signals would you expect to see in the 13 C NMR spectrum (proton-decoupled) of the following compound? Br CH 2 CH 3 A. 2 B. 5 C. 4 D. 6 E. 3 !
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How many signals do you expect to see in the 13 C NMR spectrum (proton decoupled) of the following compound at room temperature? A. 2 B. 5 C. 4 D. 6 E. 3 CH 3 H 3 C CH 3 !
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4 The molecular formula of Compound X is C 8 H 8 O 2 and it shows 13 C NMR signals at 173, 141, 133, 132, 131, 128, 126 and 22 ppm. Identify which of the structures below corresponds to Compound X. !
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5
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Alkyl Halides, Nucleophilic Substitution
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7 Three components are necessary in any substitution reaction. Substitution Reactions
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Substitution reactions are affected by the leaving group
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9 In a nucleophilic substitution reaction of R–X, the C–X bond is heterolytically cleaved, and the leaving group departs with the electron pair in that bond, forming X: ! . The more stable the leaving group X: ! , the better able it is to accept an electron pair. For example, H 2 O is a better leaving group than HO ! because H 2 O is a weaker base. The Leaving Group
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The weaker the base, the better it is as a leaving group
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11 Good Leaving Groups
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12 Poor Leaving Groups Conjugate bases of weaker acids are poorer leaving groups.
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13 Three components are necessary in any substitution reaction. Substitution Reactions
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Nucleophiles and bases are structurally similar: both have a lone pair or a ! bond. They differ in what they attack. Bases attack protons. Nucleophiles attack other electron-deficient atoms (usually carbons). Nucleophiles and Bases
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Lecture19CHM233(10)final - Organic Chemistry, Third Edition...

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