Chapter 20: Problem 11
Propose a mechanism for the following Cope rearrangement.
Chapter 20: Problem 11
Propose a mechanism for the following Cope rearrangement.
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Get started for freeEstimate the stabilization gained as a result of conjugation when 1,4 -pentadiene is converted to trans-1,3-pentadiene. Note that the answer is not as simple as comparing the heats of hydrogenation of 1,4 -pentadiene and trans-1,3-pentadiene. Although the double bonds are moved from unconjugated to conjugated, the degree of substitution of one of the double bonds is also changed, in this case from a monosubstituted double bond to a trans disubstituted double bond. To answer this question, you must separate the effect that is the result of conjugation from that caused by a change in the degree of substitution.
Claisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads to the formation of a para-substituted product. Propose a mechanism for the following rearrangement.
Treatment of anthranilic acid with nitrous acid gives an intermediate, \(\mathbf{A}\), that contains a diazonium ion and a carboxylate group. When this intermediate is heated in the presence of furan, a bicyclic compound is formed. Propose a structural formula for compound \(\mathrm{A}\) and a mechanism for the formation of the bicyclic product.
1,3-Butadiene is a gas at room temperature and requires a gas-handling apparatus to use in a Diels-Alder reaction. Butadiene sulfone is a convenient substitute for gasheated above its boiling point of \(110^{\circ} \mathrm{C}\), decomposes by a reverse Diels-Alder reaction to give s-cis-1,3-butadiene and sulfur dioxide. Draw Lewis structures for butadiene sulfone and \(\mathrm{SO}_{2}\); then, show by curved arrows the path of this reaction, which resembles a reverse Diels-Alder reaction.
Wavelengths in ultraviolet-visible spectroscopy are commonly expressed in nanometers; wavelengths in infrared spectroscopy are sometimes expressed in micrometers. Carry out the following conversions. (a) \(2.5 \mu \mathrm{m}\) to nanometers (b) \(200 \mathrm{~nm}\) to micrometers
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