Chapter 23: Problem 35
How could IR spectroscopy be used to detect the presence of enol tautomers?
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Chapter 23: Problem 35
How could IR spectroscopy be used to detect the presence of enol tautomers?
These are the key concepts you need to understand to accurately answer the question.
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Capsaicin, the spicy component of hot peppers, can be prepared from amine \(\mathbf{X}\) and acid chloride Y. Devise a synthesis of \(\mathbf{Y}\) from (4E)-6-methyl-4-hepten-1-ol \(\left[\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}=\mathrm{CH}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{OH}\right], \mathrm{CH}_{2}\left(\mathrm{CO}_{2} \mathrm{Et}\right)_{2}\), and any required inorganic reagents.
Convert acetophenone \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCH}_{3}\right)\) into each of the following compounds. You may use any other organic compounds on required inorganic reagents. More than one step may be required.
Explain why the \(\alpha\) protons of an ester are less acidic than the \(\alpha\) protons of a ketone by \(\sim 5 \mathrm{pK}_{\mathrm{a}}\) units.
Explain why each of the following carboxylic acids cannot be prepared by a malonic ester synthesis: (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{COOH} ;\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{COOH} ;\) (c) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCOOH}\).
Synthesize each compound from diethyl malonate. You may use any other organic or inorganic reagents.
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