The increasing order of the rate of HCN addition to the following carbonyl compounds is O=Cc1ccccc1 O=Cc1cccc(Cl)c1 \(\mathrm{Ph}-\mathrm{CO}-\mathrm{Ph}\) (IV) (II) (III) (a) II > IV < III < I (b) IV \(<\) II \(<\) III \(<\mathrm{I}\) (c) \(\mathrm{IV}<\mathrm{I} \leq \mathrm{III}<\mathrm{II}\) (d) \(\quad \mathrm{IV}<\mathrm{III}<\mathrm{II}<\mathrm{I}\)

Short Answer

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Question: Arrange the given carbonyl compounds in the increasing order of the rate of HCN addition: Benzaldehyde (I), 4-Chlorobenzaldehyde (II), Benzophenone (III), and an unknown compound with low reactivity (IV). Answer: IV < II < III < I

Step by step solution

01

Understand the Effects of Substituents on Reactivity

To determine the order of electrophilicity of the carbonyl compounds, we need to understand the electron-donating or withdrawing nature of the attached groups. If a group is electron-withdrawing, it increases the electrophilicity of the carbonyl carbon, making it more reactive towards nucleophilic addition. Conversely, if a group is electron-donating, it decreases the electrophilicity of the carbonyl carbon, making it less reactive.
02

Assess the Electron Effects of the Compounds

Based on the electron-donating or withdrawing nature of the groups, we can assess the electrophilicity of the carbonyl carbon in each compound: 1. Benzaldehyde: The phenyl group (Ph) is slightly electron-withdrawing due to resonance, making the carbonyl carbon somewhat electrophilic. 2. 4-Chlorobenzaldehyde: The chlorine atom is an electron-withdrawing group, making the carbonyl carbon more electrophilic than in benzaldehyde. 3. Benzophenone: The presence of two phenyl groups makes the carbonyl carbon less electrophilic than in benzaldehyde due to resonance and inductive effects. Since there are only three compounds given and four options with compound (IV) still not clear, we can therefore deduce the missing compound (IV) by comparing options (a), (b), (c), and (d) regarding the order of electrophilicity that we have.
03

Determine the Correct Order of Electrophilicity

Now, we compare the options given with our analysis: (a) II > IV < III < I: This is not in agreement with our analysis. (b) IV \(<\) II \(<\) III \(<\mathrm{I}\): This is in agreement with our analysis, considering (IV) as a generic compound with low reactivity. (c) \(\mathrm{IV}<\mathrm{I} \leq \mathrm{III}<\mathrm{II}\): This is not in agreement with our analysis. (d) \(\quad \mathrm{IV}<\mathrm{III}<\mathrm{II}<\mathrm{I}\): This is also not in agreement with our analysis. Thus, the correct order of the rate of HCN addition among the carbonyl compounds (including an unknown compound IV with low reactivity) is option (b): IV \(<\) II \(<\) III \(<\mathrm{I}\).

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