Chapter 18: Q52P (page 970)
Show how you would synthesize the following derivatives from appropriate carbonyl compounds
Short Answer
a.
b.
c.
d.
e.
f.
Chapter 18: Q52P (page 970)
Show how you would synthesize the following derivatives from appropriate carbonyl compounds
a.
b.
c.
d.
e.
f.
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Get started for freeThe Wittig reaction is useful for placing double bonds in less stable positions. For example, the following transformation is easily accomplished using a Wittig reaction
Propose a mechanism for the acid-catalyzed hydrolysis of cyclohexanone dimethyl acetal.
Two structures of the sugar fructose are shown next. The cyclic structure predominates in aqueous solution.
(a). Number the carbon atoms in the cyclic structure. What is the fuctional group at C2 in the cyclic form?
(b). Propose a mechanism for the cyclization, assuming a trace of acid is present.
Fructose fructose
(cyclic form)
Predict the products formed when cyclopentanecarbaldehyde reacts with the following reagents.
(a) PhMgBr, then H3O+
(b) Tollens reagent
(c) semicarbazide and weak acid
(d) excess ethanol and acid
(e) propane-1-3-diol, H+
(f) zinc amalgam and dilute hydrochloric acid
Sodium triacetoxyborohydride, , is a mild reducing agent that reduces aldehydes 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.
(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride.
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