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CHM233 part 3 - Organic Chemistry Third Edition Janice...

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1 Organic Chemistry, Third Edition Janice Gorzynski Smith University of Hawai’i Chapter 8 Alkyl Halides and Elimination Reactions
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2 Which of the following carbocations is most stable? CH 2 A B C D E At least two of them have similar stability, so it is impossible to determine !
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3 Relative stability of carbocations
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4 Which of the following is the strongest nucleophile in polar aprotic solvents? A) NH 2 B) OH C) Br D) CH 3 E) H 2 O !
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Summary
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6 Which of the following is the strongest nucleophile in polar protic solvents? A) F B) Cl C) HO D) CH 3 S E) CH 3 O !
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7 In which of the following solvents or solvent mixtures would an S N 1 reaction proceed most rapidly? !
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8 What is the substitution product of the reaction shown below? !
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9 Indicate which reaction proceeds the fastest. !
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10 Elimination reactions involve the loss of elements from the starting material to form a new ! bond in the product. General Features of Elimination E 2 and E 1 mechanisms
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11 In both example reactions a base removes the elements of an acid, HX, from the organic starting material. Elimination of HX
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12 Removal of the elements HX is called dehydrohalogenation. Dehydrohalogenation is an example of " elimination. The curved arrow formalism shown below illustrates how four bonds are broken or formed in the process. Dehydrohalogenation
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13 The most common bases used in elimination reactions are negatively charged oxygen compounds, such as HO !
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