Indietro
Problema 1a
Give the IUPAC name and (if possible) a common name for each compound.
(a)
Problema 1a,b
Draw the structure for each of the following:
a. 2-phenylhexane
b. benzyl alcohol
Problema 1b
Give the IUPAC name and (if possible) a common name for each compound.
(b)
Problema 1c,d
Draw the structure for each of the following:
c. 3-benzylpentane
d. bromomethylbenzene
Problema 1c
Give the IUPAC name and (if possible) a common name for each compound.
(c)
Problema 3
Why were no products from the McLafferty rearrangement observed in the spectrum of butan-2-one (Figure 18-3)?
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Problema 4d(3,4)
Give the structure of the principal product(s) when each of the following alcohols reacts with (3) DMP and (4) 1 equiv NaOCl-TEMPO.
d. 1-methylcyclohexan-1,4-diol
Problema 6
Show how you would synthesize each compound from starting materials containing no more than six carbon atoms.
Problema 7a
Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.
(a)
Problema 7b
Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.
(b)
Problema 7c
Show how you would accomplish the following synthetic
conversions by adding an organolithium reagent to an acid.
(c) pentanoic acid → heptan-3-one
Problema 7d
Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.
(d) phenylacetic acid → 3,3-dimethyl-1-phenylbutan-2-one
Problema 8
Predict the products of the following reactions.
(c) benzyl bromide + sodium cyanide
Problema 8d
Predict the products of the following reactions.
(d) product of (c) + cyclopentylmagnesium bromide, then acidic hydrolysis
Problema 8e
Predict the products of the following reactions.
(e) product of (c) + DIBAL-H, then hydrolysis
Problema 9a,b
Show how the following transformations may be accomplished in good yield. You may use any additional reagents that are needed.
(a) bromobenzene → propiophenone
(b) CH3CH2CN → heptan-3-one
Problema 9c,d
Show how the following transformations may be accomplished in good yield. You may use any additional reagents that are needed.
(c) benzoic acid → phenyl cyclopentyl ketone
(d) 1-bromohept-2-ene → oct-3-enal
Problema 10a,b
Predict the products of the following reactions:
(a)
(b)
Problema 10c,d
Predict the products of the following reactions:
(c)
(d)
Problema 10e,f
Predict the products of the following reactions:
(e)
(f)
Problema 11a
Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.
(a)
Problema 11b
Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.
(b)
Problema 11d
Show how you would accomplish the following synthetic conversions. You may use any additional reagents and solvents you need.
(d)
Problema 12a
Sodium triacetoxyborohydride, NaBH(OAc)3, is a mild reducing agent that reduces aldehydes much more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones, such as in the following reaction:
(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.
Problema 12b
Sodium triacetoxyborohydride, NaBH(OAc)3, is a mild reducing agent that reduces aldehydes much more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones, such as in the following reaction:
(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride.
Problema 13a
Propose mechanisms for
(a) the acid-catalyzed hydration of chloral to form chloral hydrate.
Problema 13b
Propose mechanisms for
(b) the base-catalyzed hydration of acetone to form acetone hydrate.
Problema 15
Propose a mechanism for each cyanohydrin synthesis just shown.
Problema 16a
Show how you would accomplish the following syntheses.
(a) acetophenone → acetophenone cyanohydrin
Problema 16b
Show how you would accomplish the following syntheses.
b. cyclopentanecarbaldehyde → 2-cyclopentyl-2-hydroxyacetic acid
