Advertisements
Advertisements
Question
An aromatic compound ‘A’ on treatment with aqueous ammonia and heating forms compound ‘B’ which on heating with Br2 and KOH forms a compound ‘C’ of molecular formula C6H7N. Write the structures and IUPAC names of compounds A, B and C.
Advertisements
Solution
It is given that compound ‘C’ having the molecular formula C6H7N is formed by heating compound ‘B’ with Br2 and KOH. This is a Hoffmann bromamide degradation reaction. Therefore, compound ‘B’ is an amide and compound ‘C’ is an amine. The only amine having the molecular formula C6H7N is aniline (C6H5NH2).
Therefore, compound ‘B’ (from which ‘C’ is formed) must be benzamide (C6H5CONH2).
Further, benzamide is formed by heating compound ‘A’ with aqueous ammonia. Therefore, compound ‘A’ must be benzoic acid.
The given reactions can be explained with the help of the following equations:
APPEARS IN
RELATED QUESTIONS
Convert 3-Methylaniline into 3-nitrotoluene.
Write the IUPAC name of the following compound and classify it as primary, secondary and tertiary amine.
CH3NHCH(CH3)2
Write the IUPAC name of the following compound and classify it as primary, secondary and tertiary amine.
(CH3)3CNH2
Give one chemical test to distinguish between the following pair of compounds.
Aniline and N-methylaniline
Account for the following:
pKb of aniline is more than that of methylamine.
Account for the following:
Ethylamine is soluble in water, whereas aniline is not.
Account for the following:
Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.
How will you convert methanamine into ethanamine?
How will you convert propanoic acid into ethanoic acid?
Accomplish the following conversion:
Benzoic acid to aniline
Complete the following reaction:
\[\ce{C6H5N2Cl + C2H5OH ->}\]
Complete the following reaction:
\[\ce{C6H5NH2 + (CH3CO)2O ->}\]
Do the following conversions in not more than two steps :
Propanone to Propene
How are ethylamine and ethyl methyl amine distinguished by using nitrous acid?
Write the IUPAC name of the given compound :
Give simple chemical tests to distinguish between the following pair of compounds:
Benzaldehyde and Benzoic acid
Do the following conversions in not more than two steps:
\[\begin{array}{cc}
\ce{CH3CN to CH3 - C - CH3}\\
\phantom{...........}||\\
\phantom{...........}\ce{O}
\end{array}\]
Do the following conversions in not more than two steps:
