Chapter 16: Problem 11
Complete the equations for these oxidations. (a) \(\mathrm{Hexanal}+\mathrm{H}_{2} \mathrm{O}_{2} \longrightarrow\) (b) 3 -Phenylpropanal \(+\) Tollens' reagent \(\longrightarrow\)
Chapter 16: Problem 11
Complete the equations for these oxidations. (a) \(\mathrm{Hexanal}+\mathrm{H}_{2} \mathrm{O}_{2} \longrightarrow\) (b) 3 -Phenylpropanal \(+\) Tollens' reagent \(\longrightarrow\)
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Get started for freeTreatment of \(\beta\)-D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the - \(\mathrm{OH}\) on carbon 1 is transformed into an \(-\mathrm{OCH}_{3}\) group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.
A primary or secondary alcohol can be protected by conversion to its tetrahydropyranyl ether. Why is formation of THP ethers by this reaction limited to primary and secondary alcohols?
Both (S)-citronellal and isopulegol are naturally occurring terpenes (Section 5.4). When (S)-citronellal is treated with tin(IV) chloride (a Lewis acid) followed by neutralization with aqueous ammonium chloride, isopulegol is obtained in \(85 \%\) yield. (a) Show that both compounds are terpenes. (b) Propose a mechanism for the conversion of (S)-citronellal to isopulegol. (c) How many stereocenters are present in isopulegol? How many stereoisomers are possible for a molecule with this number of stereocenters? (d) Isopulegol is formed as a single stereoisomer. Account for the fact that only a single stereoisomer is formed.
If the Favorskii rearrangement of 2-chlorocyclohexanone is carried out using sodium ethoxide in ethanol, the product is ethyl cyclopentanecarboxylate. Propose a mechanism for this reaction.
Starting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary. (a) Cyclohexanol (b) Cyclohexene (c) cis-1,2-Cyclohexanediol (d) 1 -Methylcyclohexanol (e) 1-Methylcyclohexene (f) 1 -Phenylcyclohexanol (g) 1-Phenylcyclohexene (h) Cyclohexene oxide (i) trans-1,2-Cyclohexanediol
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