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Q.

(i) Write the final products in the following
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(ii) Arrange the following in the increasing order of their reactivity towards nucleophilic addition, reaction
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(iii) Draw the structure of 2, 4-DNP derivative of acetaldehyde.

OR

Generalize about the relationship of basicity and nucleophilicity from the following relative rates of nucleophilic displacements:
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Detailed Solution

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(ii) As the number and size of the substituted group increases, the hindrance to the attack of nucleophile also increases. Hence, the order of nucleophilic addition C 
C5H6COCH3<CH3COCH3<CH3CHO<HCHO
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OR

(a) Bases are better nucleophiles than their conjugate acids.
(b) In going from left to right across the periodic table, basicity and nucleophilicity decrease.
(c) In going down a group in the periodic table nucleophilicity increases while basicity decreases.
(d) If the nucleophilic and basic sites are on the same atom (here an O), nucleophilicity parallels basicity.
(e) Relative rates are counter to relative basicity's. When the atom bonded to the nucleophilic site also has an unshared pair of eˉ, e.g., G—Nu: nucleophilicity of the species increases.

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