4.28 quiz - TABLE ONE Rates of S N 1 reaction as you change...

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Weekly Quiz April 28, 2006 1. The leaving group does play a role in the likelihood of the reaction. Which one of these two reactions is likely to proceed forward, and which one is not? Why? Draw reaction coordinate diagrams for these reactions. NH 2 NaOH DMSO OH O NaCl Cl HMPA S O O 2. Go back and consider the following reactions (you know these!) and suggest the mechanism it likely proceeds by. What evidence do you have to support this? a. Reaction of SOCl 2 with a secondary alcohol (shown below)
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OH S O Cl Cl HO S O Cl + NH 3 O S O Cl Cl - Cl + -OSCl O release SO 2 and Cl - b. Reaction of a vicinal dibromide with strong base. c. Reaction of an alkynl anion with a primary alkyl halide. d. Reaction of a tertiary alcohol with HX. 3. What is the product? What mechanism has the reaction proceeded by?
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Br CH 3 OH Br NaCN HMPA OTos NaOCH 3 CH 3 OH Br NaSCH 3 DMSO 4. What are the ideal conditions to make the following conversions.
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CH 2 CH 3 NH 2 CH 2 CH 3 Br I CN Br 5. Explain the effect changes in solvent play in S N 1 and S N 2 reactions by looking at the data in the following two tables.
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Unformatted text preview: TABLE ONE Rates of S N 1 reaction as you change the dielectric constant of the solvent. Solvent Dipole moment, μ Dielectric constant, ε Relative Rate CH 3 CO 2 H 1.68 6 1 CH 3 OH 2.87 33 4 H 2 O 1.84 78 150,000 Dipole moment, μ in debye TABLE TWO Rates of S N 2 reaction as you change the type of solvent (protic v. aprotic) Solvent Dipole moment, μ Dielectric constant, ε Relative Rate Type CH 3 OH 2.87 33 1 protic H 2 O 1.84 78 7 protic DMSO 3.96 49 1,300 aprotic DMF 3.82 37 2,800 aprotic CH 3 CN 3.92 38 5,000 aprotic 6. Synthesis CN Br SH OCH 3 7. Which isomer reacts faster via an E2 mechanism— cis-1-bromo-3-isopropylcyclohexane or trans-1-bromo-3-isopropylcyclohexane? Why? 8. Show the E2 elimination product from this molecule: Br H H 3 C CH 3 H 3 CH 2 C H 9. How would you synthesize these molecules from a nucleophile and an alkyl halide: O SH a. b....
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This note was uploaded on 04/20/2008 for the course CHEM 231 taught by Professor Montaguesmith during the Spring '06 term at Maryland.

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4.28 quiz - TABLE ONE Rates of S N 1 reaction as you change...

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