List the following compounds in order of increasing basicity (least to most), an

Question

List the following compounds in order of increasing basicity (least to most), and explain your reasoning. Outline the steps involved in the Gabriel synthesis of 3-amino-2-methylpentane. Outline the steps involved in the synthesis of 4-bromo-3-nitro-phenol from 4 bromobenzoic acid Please give the major product and a mechanism for its formation in the following reaction. H_3O^+ Draw the structure of the product likely to be obtained from the reaction between acetoacetic ester, bromobenzene and 2 molar equivalents of sodium amide (in liquid ammonia)? Give a mechanism for its formation.

Explanation / Answer

ANSWER: The order of basicity from least to most is structure (II) , ( III) and ( I)

Because in structure (II) the   -NH- group donates electron to the double bond and hence its eleetron donating capacity decreases,

where as in -NH2- group of structure (III) the lone pair of electorn on nitrogen atom can be donated.

     In structure (I), the -CN- group contains lone pair of electron and nitrogen is more electronegative than carbon hence it pulls the electron towards itself thus increasing the electron donating capacity.

Hence order is CH3-CH=NH< CH3-CH2-NH2 < CH3-CH2-CN [ From Lewis theory, which states that base is a donor of electron pair.]

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