Chapter 18: Q22P (page 947)
Predict the products of the following reactions.
Chapter 18: Q22P (page 947)
Predict the products of the following reactions.
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Get started for freeShow how you would accomplish the following syntheses efficiently and in good yield. You may use any necessary reagents.
(a)
(b)
(c)
(d)
(e)
(f)
(g)
Draw the structures of the following derivatives.
(a) the 2,4-dinitrophenylhydrazone of acetone
(b) the semicarbazone of cyclopentanone
(c) cyclcobuanone oxime
(d) the ethylene acetal of hexan-2-one
(e) acetaldehyde diethyl acetal
(f) the ethyl hemiacetal of acetaldehyde
(g) the (Z) isomer of the ethyl imine of propiophenone
(h) the hemiacetal form of 6-hydroxyhexanal
In the absence of water, o-phthalaldehyde has the structure shown. Its strongest IR absorption is at 1687 cm-1;the proton NMR data are shown by the structure. In the presence of water, a new compound is formed that has a strong IR absorption around 3400 cm-1and no absorption in the C=0 region. Propose a structure of X consistent with this information and suggest how X was formed.
Why were no products from McLafferty rearrangement observed in the spectrum of butan-2-one?
The family of macrolide antibiotics all have large rings (macrocycle) in which an ester is what makes the ring; a cyclic ester is termed as a lactone. One example is amphotericin B, used as an anti-fungal treatment of last resort because of its liver and heart toxicity. Professor Martin Burke of the University of Illnois has been making analogs to retain the antifungal properties but without the toxicity, including this structure published in 2015. (Nature Chemical Biology, (2015) doi: 10.1038/nchembio.1821). The carboxylate of amphotericin B has been replaced with the urea group (shown in red).
(a) Where is the lactone group that forms the ring?
(b) Two groups are circled. What type of functional group are they? Explain.
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