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Chapter 11: Problem 228

Give structures and names of the principal organic products expected from the monosulfonation of: (a) cyclohexylbenzene (d) m-nitrophenol (b) benzenesulfonic acid (e) o-fluoroanisole (c) salicylaldehyde (f) o-nitroacetanilide \(\left(\mathrm{O}-\mathrm{HOC}_{6} \mathrm{H}_{4} \mathrm{CHO}\right) \quad\left(\mathrm{o}-\mathrm{O}_{2} \mathrm{NC}_{6} \mathrm{H}_{4} \mathrm{NHCOCH}_{3}\right)\) (g) o-xylene

Short Answer

Expert verified
The principal organic products of the monosulfonation are: (a) 2-cyclohexylbenzenesulfonic acid (b) 3-benzenesulfonic acid (c) 5-formyl-2-hydroxybenzenesulfonic acid (d) 2-nitro-4-hydroxybenzenesulfonic acid (e) 3-fluoro-5-methoxybenzenesulfonic acid (f) 3-nitro-N-acetylaniline-5-sulfonic acid (g) 4,5-dimethylbenzenesulfonic acid

Step by step solution

01

a) Cyclohexylbenzene

For cyclohexylbenzene, the cyclohexyl group is an activating group; therefore, sulfonation will occur either at the ortho position (C2) or the para position (C4). As the ortho position is more accessible and the steric hindrance is low, the primary product will be an ortho-substituted compound. In this reaction, the main product of cyclohexylbenzene monosulfonation will be 2-cyclohexylbenzenesulfonic acid.
02

b) Benzenesulfonic acid

The sulfonic acid group is an electron-withdrawing group, making it deactivating. The reaction will occur predominantly at the meta position (C3) since sulfonic acid is meta-directing. The primary product will be 3-benzenesulfonic acid.
03

c) Salicylaldehyde

Salicylaldehyde has two substituents: the hydroxy group (OH) and the aldehyde group (CHO). The hydroxy group is an activating group, while the aldehyde group is a deactivating group. The hydroxy group will dominate since it is much more activating than the aldehyde group is deactivating. Therefore, sulfonation will occur at the ortho position to the OH group and para to the CHO group. The primary product will be 5-formyl-2-hydroxybenzenesulfonic acid.
04

d) m-Nitrophenol

In the case of m-nitrophenol, the nitro group is a deactivating group and is in meta position relative to the hydroxy group. Sulfonation will occur predominantly at the para position to the hydroxy group (C4) since hydroxyl is activating (ortho- and para-directing) and nitro group is deactivating (meta-directing). The primary product will be 2-nitro-4-hydroxybenzenesulfonic acid.
05

e) o-Fluoroanisole

For o-fluoroanisole, the methoxy group (-OCH3) is an activating group, while the fluoro group (-F) is slightly deactivating. The methoxy group dominates and directs the sulfonation mainly to its ortho position (C3). The primary product will be 3-fluoro-5-methoxybenzenesulfonic acid.
06

f) o-Nitroacetanilide

O-nitroacetanilide has a nitro group, which is a deactivating group. Sulfonation will occur predominantly at the meta position (C5) relative to the C1 position. The deactivation is more significant than the small activating effect of the acetamide group. The primary product will be 3-nitro-N-acetylaniline-5-sulfonic acid.
07

g) o-Xylene

O-xylene is a disubstituted benzene with two methyl (-CH3) groups on adjacent (ortho) positions. Sulfonation will occur at the para position to one of the methyl groups (C4), considering that methyl groups are activating and ortho- and para-directing. The primary product will be 4,5-dimethylbenzenesulfonic acid.

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Most popular questions from this chapter

(a) The bromination of benzene is catalyzed by small amounts of iodine. Consider a possible explanation for this catalytic effect. (b) The kinetic expression for the bromination of naphthalene in glacial acetic acid involves a term that is first order in naphthalene and second order in bromine. Consider how two molecules of bromine and one of naphthalene could be involved in the rate-determining step of bromination. Suggest a reason why the kinetic expression simplifies to first order in naphthalenes and first order in bromine in 50 per cent aqueous acetic acid.

Arrange the following in order of reactivity toward ring nitration, listing by structure the most reactive at the top, the least reactive at the bottom. (a) benzene, mesitylene \(\left[1,3,5-\mathrm{C}_{6} \mathrm{H}_{3}\left(\mathrm{CH}_{3}\right)_{3}\right]\), toluene, m-xylene, p-xylene (b) acetanilide \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHCOCH}_{3}\right)\), acetophenone \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCH}_{3}\right)\), aniline, benzene (c) \(2,4-\) dinitrochlorobenzene, 2,4 -dinitrophenol.

Starting with the definition of partial rate factor, derive an expression relating \(\mathrm{p}^{\mathrm{G}} \mathrm{f}\) to the rate of substitution para to \(\mathrm{G}\) in \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{G}\).

\(2,2^{\prime}-\) Dinitrobiphenyl is to be synthesized. Outline the method of preparation from iodobenzene. No other organic reagent may be used. Any inorganic reagent may be employed.

Draw the principal resonance forms of the nitronium ion.
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