Chapter 15: 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 15: 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 freeIn Section 11.5, we saw that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?
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
(R)-Pulegone, readily available from pennyroyal oil, is an important enantiopure building block for organic syntheses. Propose a mechanism for each step in this transformation of pulegone.
Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four-membered, five-membered, or six-membered ring. When D-ribose is treated with methanol in the presence of an acid catalyst, two cyclic acetals, \(\mathrm{A}\) and \(\mathrm{B}\), are formed, both with molecular formula \(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}_{5}\). These are separated, and each is treated with sodium periodate (Section 10.8C) followed by dilute aqueous acid. Both \(\mathrm{A}\) and \(\mathrm{B}\) yield the same three products in the same ratios.
When cis-2-decalone is dissolved in ether containing a trace of \(\mathrm{HCl}\), an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture.
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