PracticeQuestionsChap8-10

PracticeQuestionsChap8-10 - Chem 2261 Checklist and...

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1 Chem 2261 Checklist and Practice Questions for Chapters 8-10 Chapter 8 ± Rank alkyl halide substrates in order of reactivity in an S N 2 (or S N 1) reaction. ± Rank nucleophiles in order of reactivity in an S N 2 (or S N 1) reaction. ± Rank leaving groups in order of reactivity in an S N 2 (or S N 1) reaction. ± Rank solvents in terms of effectiveness (reaction rate) in an S N 2 (or S N 1) reaction. ± Draw and/or explain products (including stereochemical outcome where appropriate) an S N 2 (or S N 1) reaction. ± Distinguish between substrates and/or reaction conditions likely to favor the S N 2 or S N 1 mechanism for nucleophilic substitution. ± Carbocation Stability ± Carbocation Rearrangement. Chapter 9 ± Draw and/or explain products (including selectivity where appropriate) an E2 (or E1) reaction. ± Types of Selectivity ± Regioselectivity ± Reactions which follow Zaitsev's Rule (i.e., give the more stable alkene product). ± Exceptions to Zaitsev's Rule (for example: alkyl fluorides). ± Stereoselectivity ± Consequences of requirement for C-H and C-X to be antiperiplanar in E2 reactions. ± Distinguish between substrates and/or reaction conditions likely to favor substitution (S N 2 or S N 1) or elimination (E2 or E1). Chapter 10 ± Nomenclature of alcohols ± Conversion of alcohols to alkyl halides ± By reaction with HX ± By reaction with PBr 3 , PCl 3 , or SOCl 2 . ± Conversion of alcohols to alkyl tosylates (ROH to ROTs). ± Controlling stereochemistry for nucleophilic substitution reactions involving secondary alcohols. ± Conversion of an alcohol to a halide (using PBr 3 , PCl 3 , or SOCl 2 ) occurs with inversion of configuration (because oxygen of alcohol gets displaced in S N 2 reaction). ± Conversion of an alcohol to a sulfonate ester occurs with retention of configuration (because carbon- oxygen bond of alcohol retained; no S N 2 displacement) ± Dehydration (conversion of alcohols to alkenes) ± 3° alcohols are more reactive (room temp. reaction) and 1° and 2° alcohols (which require heating) ± 2° and 3° alcohols undergo S N 1 ( look for carbocation rearrangement) ± 1° undergo S N 2 ( no carbocation rearrangement possible) ± Formation of Ethers ± Williamson Ether Synthesis (S N 2 reaction of an alkoxide) ± Identify preferred alkyl halide/alkoxide combination for synthesis of an unsymmetrical ether. ± Via carbocation intermediates ± Formation of epoxides from halohydrins ± Nucleophilic substitution reactions of epoxides ± Ring-Opening under Basic Conditions ± Regiochemistry = Nucleophile adds to less substituted side ± Ring-Opening under Acidic Conditions ± Regiochemistry = Nucleophile adds to more substituted side ± Stereochemistry = inversion of configuration for either type of epoxide ring-opening.
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Practice Questions for Chapters 8-10 2 1. Indicate (circle) the substrate in each of the following groups which is most reactive under the reaction conditions given. (Chapter 8) MeOH NaSH NaI H 2 O acetone or heat Cl a) b) c) d) 2.
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This note was uploaded on 04/21/2010 for the course CHEM 2261 taught by Professor Crowe during the Fall '08 term at LSU.

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PracticeQuestionsChap8-10 - Chem 2261 Checklist and...

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