stock solutions: 1. Phenol 2. Anisole 3. Diphenyl ether 4. Acetanilide 5. 4-brom

Question

stock solutions:

1. Phenol

2. Anisole

3. Diphenyl ether

4. Acetanilide

5. 4-bromo-phenol

2. Compare the reactivity of the stock solutions TABLE 232 Relative Rates of Nitration with the expected order of reactivity for these compounds using Table 23-2 (provided) Specifically highlight how the experimental reaction rate compares to the theoretical relative reaction rates for nitration from Table 23-2 for each starting material. Explain any deviations or unexpected results. of Monosubstituted Benzenes So, H.SO Type of Group Strongly activating StrorwJy activating Weakly activating Relative Rate N/A OH 1000 25 1 (referenice) 0.18 0.033 Weakly deactivating Wankly deactivating Moderately vatng Strongly deactivating Strongly deactivating CI 0.0037 6 x 10 1.2 x 10 Asomatic amines are susceptible to protonation and axidason under nitration conditions. The Ni, group is

Explanation / Answer

Ans:

The expected decreasing order of reactivity of given stock solutions for nitration is as following.

Reactivity towards nitration: Phenol>4-bromo-phenol>Anisole>diphenylether>acetanilide.

Figure 1. A) Resonance structures of phenol (strongly activating group; in this case benzene ring is electron rich due to donation of loan pair of electrons by oxygen). B) Resonance structures of nitrobenzene (strongly deactivating group; in this case benzene ring is electron poor due to withdrawing nature of -electrons of benzene by nitro group)

For better understanding chemical structures of given compounds are provided below.

   

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