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UK CHE 230 - Homework

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Homework problems –Chapters 6 and 7 1. Give the curved-arrow formalism for the following reaction: H3C O -+H CH2HCCH3Br:::CH3O HH2CCHCH3Br-++ 2. In each of the following sets, arrange the compounds in order of decreasing pKa and explain your reasoning. (a) ClCH2CH2SH, ClCH2CH2OH, CH3CH2OH (b) CH3O—CH2—COOH, CH3—COOH, CH3OCH2—CH(OCH3)—COOH (c) CH3CH2OH, (CH3)2N—CH2CH2OH, (CH3)3N+—OH (d) CH3CH2CH2COOHCl—CH2CH2CH2COOHCH2COOHH3CHCClHC COOHCH3CH2Cl 3. Rank the following compounds in order of increasing basicity: CH3COO-CH3CONH-CH2COO-H3N+ 4. In each pair, choose the species that reacts more rapidly with methyl bromide in ethanol solvent, and explain your choices (a) –OC2H5 or C2H5OH (b) F- or I- 5. In each pair, choose the combination of nucleophile and solvent that would give the faster SN2 reaction with ethyl iodide (a) Na+ –OAc in formamide, or Na+ –OAc in DMF (b) Na+ –OAc in acetic acid, or Na+ –OAc in DMF -OAc = CH3COO- 6. Choose the alkyl halide(s) from the following list of C6H13Br isomers that meet each criterion below:(1) 1-bromohexane (2) 3-bromo-3-methylpentane (3) 1-bromo-2,2-dimethylbutane (4) 3-bromo-2-methylpentane (5) 2-bromo-3methylpentane (a) the compound that gives the fastest SN2 reaction with sodium methoxide (b) the compound that is least reactive to sodium methoxide in methanol (c) the compound(s) that give only one alkene in the E2 reaction (d) the compound(s) that give an E2 but no SN2 reaction with sodium methoxide in methanol (e) the compound(s) that undergo an SN1 reaction to give rearranged products (f) the compound that gives the fastest SN1 reaction 7. Give the products expected when 1-bromo-3-methylbutane reacts with the following reagents: (a) KI in aqueous acetone (b) KOH in aqueous ethanol (c) K+ t-Bu—O- on t-BuOH 8. Give the products expected when 2-bromo-2-methylhexane reacts with the following reagents: (a) KI in aqueous acetone (b) Sodium ethoxide in ethanol (c) 1:1 ethanol-water 9. Rank the following compounds in order of increasing SN2 reaction rate with KI in acetone. (a) methyl bromide (b) sec-butyl bromide (c) 3-(bromomethyl)-3-methylpentane (d) 1-bromopentane (e) 1-bromo-2-methylpentane 10. Give all of the product(s) expected, with pertinent stereochemistry, when each of the following compounds reacts with sodium ethoxide in ethanol 11. (a) (R)-2-bromopentane(b) DHBrCH3CH2CH2 12. Which of the following alkyl halides can give only one alkene, and which can give a mixture of alkene in the E2 reaction? CH3CH2CHCH2BrCH3H2CBrCBrCH3CH3(a)(b)(c) 13. Which alkyl halide and what conditions should be used to prepare the following alkene in good yield by an E2 elimination? CH2 14. What products are formed, and by what mechanisms, in each of the following cases? (a) methyl iodide and NaCN in ethanol (b) 2-bromo-3-methyl butane in ethanol (c) 2-bromo-3-methylbutane in anhydrous acetone (d) 2-bromo-3-methylbutane in ethanol containing an excess of sodium ethoxide (e) 2-bromo-2-methylbutane in ethanol containing an excess of sodium iodide (f) neopentyl bromide in ethanol containing an excess of sodium


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