Chapter 17, Problem 99AP

9.22 Propose a structure for an alcohol with molecular formula C5H12O that has the 1H NMR spectrum given in Figure

For each set of carbonyl additions, circle the carbonyl addition that occurs at the faster rate (assuming everything is the same except that the reagent/substrate differs - i.e., same temperature, and ratios/concentrations of reagent and substrate). Electrostatic attraction has a greater impact on the relative rates than steric hindrance. (a) CH3OH HO OCH3 H H CH3 i CH₂OH HO OCH 3 H F3C CH3 (b) F3C NaOCH3 HO OCH3 H3C CH3 H3C CH3 CH3OH HO OCH3 H3C CH3 H3C CH3 (c) NaSCH3 OSCH 3 H3C CH3 H3C CH3 NaOCH3 O OCH 3 H3C CH3 H3C CH3

9.34. Assign the chemical shifts and splitting patterns to specific aspects of the structure you propose. C5H12O 1H 2H 2 6H ille H(ppm) 1 3H и 0

HO (c) (1 pt) Both of the following are hydride donors. Circle the harder nucleophile of -P-Cu-H Н H-AI-H HINIH Н (d) (4 pts) The following reaction involves two steps. Draw the anionic intermediate that forms after sodium hydride reacts and the final organic product. Hints: what type of nucleophile is NaH and where does that mean it will react? Also, the second step is not a proton transfer. What's the most likely reaction for that intermediate to undergo? NaH anionic intermediate final product

Predict the product(s) for the reaction shown. O excess HBr heat

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7. Our textbook says that the fragmentation that occurs in the mass spectrometry of alkanes can be understood by realizing that "the differences in energy among ... tertiary, secondary, primary and methyl carbocations in the gas phase are much greater than the differences among comparable radicals. Therefore, where alternative modes of fragmentation are possible, the more stable carbocation tends to form in preference to the more stable radical." Given this information, which one of the following hexane isomers (all C6H14) is most likely to have a strong M-15 peak (that is, a peak at m/z 71)? HINT: You're looking for a compound that forms a 3° carbocation after loss of an electron and a CH³· radical. A) n-hexane D) 2-methylpentane B) 2,2-dimethylbutane E) 3-methylpentane C) 2,3-dimethylbutane

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