Problem
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1.
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Draw
a structure corresponding to the following name:
5,5-dimethyl-1,3-cyclohexanedione (dimedone)
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2.
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Provide the IUPAC name for the structure below.
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3.
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Provide the IUPAC name for the structure below.
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Cyanohydrins
Consider the data below to answer the following
questions.
Cyanohydrins are important intermediates in the
synthesis of a-hydroxycarboxylic acids from ketones and aldehydes. The nitrile
functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid. Nitriles can also be
hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a cyanohydrin is treated with
aqueous base the original carbonyl compound is isolated.
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4.
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Refer
to Cyanohydrins. The reaction of an aldehyde with hydrogen cyanide is an example of __________
reaction.
a. | a nucleophilic substitution | b. | an electrophilic addition | c. | an electrophilic substitution | d. | a nucleophilic addition | | |
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5.
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Refer
to Cyanohydrins. Identify the electrophile in the reaction of benzaldehyde with hydrogen
cyanide.
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Reaction 19-2
Consider the reaction below to answer the following
questions.
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6.
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Refer
to Reaction 19-2. The nucleophile in this reaction is:
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7.
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Give
the major organic product(s) for the following reaction or sequence of reactions. Show all relevant
stereochemistry.
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8.
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Give
the major organic product(s) for the following reaction or sequence of reactions. Show all relevant
stereochemistry.
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9.
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Choose the BEST reagent for carrying out the following
conversion.
A. | 1. PhMgBr, ether | | | 2. H3O+ | B. | 1. PhCH2MgBr, ether | | | 2. H3O+ | C. | (C6H5)3P=CHC6H5,
THF | D. | Li(C6H5)2Cu, ether | | |
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Compound Formula
Consider the
data below to answer the following questions.
C7H14O
IR: | 1715 cm-1 | MS: | M+ at m/z = 114, a-cleavage
fragment at m/z = 71,
McLafferty rearrangement fragment at m/z -
86. | 1HNMR: | 0.92
d (6H, triplet),
1.59 d (4H,
multiplet), 2.36 d (4H, triplet) | | |
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10.
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Refer
to Compound Formula. Interpret the 1H NMR data.
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