Chapter 12: Q21E (page 354)
Predict the product(s) and show the complete electron-pushing mechanism for each of the following dissolving metal reductions.

Short Answer
a).

b).

c).

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Chapter 12: Q21E (page 354)
Predict the product(s) and show the complete electron-pushing mechanism for each of the following dissolving metal reductions.

a).

b).

c).

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Show the structures of the fragments you would expect in the mass
spectra of the following molecules:

As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wohler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone.
(a) What is a likely structure for the keto acid?
(b) What is a likely structure for ecgonine, neglecting stereochemistry?
(c) What is a likely structure for cocaine, neglecting stereochemistry?
Question: Grignard reagents undergo a general and very useful reaction with
ketones. Methylmagnesium bromide, for example, reacts with cyclohexanoneto yield a product with the formula . What is the structure of this product if it has an IR absorption at ?

Where would you expect each of the following compounds to absorb in the IR spectrum?
(a) 4-Penten-2-one (b) 3-Penten-2-one
(c) 2,2-Dimethylcyclopentanone (d) m-Chlorobenzaldehyde
(e) 3-Cyclohexenone (f) 2-Hexenal
Question: Write molecular formulas for compounds that show the following molecular ions in their high-resolution mass spectra, assuming that C, H, N, and O might be present. The exact atomic masses are: 1.00783 , 12.00000 , 14.00307 , 15.99491 .
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