EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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When acetonitrile is treated with concentrated sulfuric acid and tert-butanol, followed by water, a product is formed
whose 'H NMR spectrum exhibits the following three signals: singlet, 1.3 ppm, 9 H; singlet, 2.0 ppm, 3 H; and
broad singlet, 8.2 ppm, 1 H. Its IR spectrum exhibits one broad absorption of medium intensity between 3300 and
3500 cm-1, and a narrow, intense absorption near 1650 cm¯1. A key intermediate is shown. Draw the structure of
the product, and draw the complete, detailed mechanism for the reaction.
CH3
CH3
H2SO4 (conc)
H2O
?
+ H3C
H3C
H3C-C=Ñ-c
`CH3
CH3
HO
(c) Treating lactone B with two equivalents of phenylmagnesium bromide, followed by hydrolysis in
aqueous acid, gives a compound with the molecular formula C18H22O2, as shown below.
Propose a structural formula for this compound.
1. PhMgBr (2 eq.)
2. H'/H>O
C18H2202
bj
1o
14
10I
f6
40
&
3
4
00
(8)
Please propose structures for ketones or aldehydes having the following 1H NMR spectra
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