Chapter 18: 18-18-7P b (page 575)
Predict the products of the following reactions:
b) The product of the reaction is,
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The red fox (Vulpesvulpes) uses a chemical communication system based on scent marks in urine. One component of fox urine is a sulfide whose mass spectrum has . IR spectroscopy shows an intense band at and NMR spectroscopy reveals the following peaks:
(, singlet); (, singlet); (, triplet, ); (, triplet, ); (, broad). Propose a structure consistent with these data. [Note: absorbs at ].Treatment of 1,1-diphenyl-1,2-epoxyethane with aqueous acid yields diphenylacetaldehyde as the major product. Propose a mechanism for the reaction.
Name the following ethers:
d)
Give IUPAC names for the following compounds (reddish brown 5 Br; yellow 5 S):
Aldehydes and ketones undergo acid-catalyzed reaction with alcoholsto yield hemiacetals,compounds that have one alcohol-like oxygenand one ether-like oxygen bonded to the same carbon. Further reactionof a hemiacetal with alcohol then yields an acetal,a compound that hastwo ether-like oxygens bonded to the same carbon.
(a)Show the structures of the hemiacetal and acetal you would obtainby reaction of cyclohexanone with ethanol.
(b)Propose a mechanism for the conversion of a hemiacetal into anacetal.
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