Chapter 21: Problem 10
Draw a structural formula for each compound. (a) 1-Nitronaphthalene (b) 1,6 -Dichloronaphthalene (c) 9-Bromoanthracene (d) 2-Methylphenanthrene
Chapter 21: Problem 10
Draw a structural formula for each compound. (a) 1-Nitronaphthalene (b) 1,6 -Dichloronaphthalene (c) 9-Bromoanthracene (d) 2-Methylphenanthrene
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Get started for freeFollowing each name is the number of Kekulé structures that can be drawn for it. Draw these Kekulé structures and show, using curved arrows, how the first contributing structure for each molecule is converted to the second and so forth. (a) Naphthalene (3) (b) Phenanthrene (5)
Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of \(\mathrm{D}\) to \(\mathrm{E}\). (d) Propose a mechanism for the conversion of \(F\) to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?
Propose a structural formula for each compound given these NMR data. (a) \(\mathrm{C}_{9} \mathrm{H}_{9} \mathrm{BrO}\) (b) \(\mathrm{C}_{\mathrm{g}} \mathrm{H}_{9} \mathrm{NO}\) (c) \(\mathrm{C}_{9} \mathrm{H}_{9} \mathrm{NO}_{3}\) $$ \begin{array}{lc} \hline{ }^{1} \text { H-NMR } & { }^{13} \text { C-NMR } \\ \hline 1.39(\mathrm{t}, 3 \mathrm{H}) & 165.73 \\ 4.38(\mathrm{q}, 2 \mathrm{H}) & 131.56 \\ 7.57(\mathrm{~d}, 2 \mathrm{H}) & 131.01 \\ 7.90(\mathrm{~d}, 2 \mathrm{H}) & 129.84 \\ & 127.81 \\ & 61.18 \\ & 14.18 \\ \hline \end{array} $$ $$ \begin{array}{lc} \hline{ }^{1} \text { H-NMR } & { }^{13} \text { C-NMR } \\ \hline 2.06(\mathrm{~s}, 3 \mathrm{H}) & 168.14 \\ 7.01(\mathrm{t}, 1 \mathrm{H}) & 139.24 \\ 7.30(\mathrm{~m}, 2 \mathrm{H}) & 128.51 \\ 7.59(\mathrm{~d}, 2 \mathrm{H}) & 122.83 \\ 9.90(\mathrm{~s}, 1 \mathrm{H}) & 118.90 \\ & 23.93 \\ \hline \end{array} $$ $$ \begin{array}{cc} \hline{ }^{1} \text { H-NMR } & { }^{13} \text { C-NMR } \\ \hline 2.10(\mathrm{~s}, 3 \mathrm{H}) & 168.74 \\ 7.72(\mathrm{~d}, 2 \mathrm{H}) & 166.85 \\ 7.91(\mathrm{~d}, 2 \mathrm{H}) & 143.23 \\ 10.3(\mathrm{~s}, 1 \mathrm{H}) & 130.28 \\ 12.7(\mathrm{~s}, 1 \mathrm{H}) & 124.80 \\ & 118.09 \\ & 24.09 \\ \hline \end{array} $$
Account for the fact that \(p\)-nitrophenol \(\left(K_{\mathrm{a}} 7.0 \times 10^{-8}\right)\) is a stronger acid than is phenol \(\left(K_{\mathrm{a}} 1.1 \times 10^{-10}\right)\).
Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.
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