Study Material

ORGANIC COMPOUNDS CONTAINING NITROGEN

Chemistry

Inter Second Year

English

Very Short Answer Questions

Q1. Write the IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines. i) $\ce{(CH3)3 CHNH2}$ ii) $\ce{CH3(CH2)2NH2}$ iii) $\ce{(CH3CH2)2 NCH3}$

Q2. Explain why ethylamine is more soluble in water whereas aniline is not soluble.

Q3. Why aniline does not undergo Friedel-Crafts reaction?

Q4. Gabriel phthalimide synthesis exclusively forms primary amines only. Explain.

Q5. Arrange the following bases in decreasing order of$\ce{ p^K_b}$, values. $\ce{C2H5NH2,\,\, C6H5NHCH3, \,\, (C2H5)2NH}$ and $\ce{C6H5NH2}$,

Q6. Arrange the following bases in increasing order of their basic strength. Aniline, p-nitroaniline and p-toluidine.

Q7. Write equations for Carbylamine reaction of any one aliphatic amine.

Q8. Give structures of A,B and C in the following reaction. CHN CI CUCN H?O/H ne 0 04 B V4

Q9. Accomplish the following conversions: i) Benzoic acid to benzamide ii). Aniline to p-bromoaniline

Q10. Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?

Short Answer Questions

Q1. Write the IUPAC names of the following compounds: i) $\ce{CH3CH2 NHCH2 CH2 CH3}$ ii). $\ce{PhCH2 CN}$

Q2. Give one chemical test to distinguish between the following pairs of compounds. i) Methylamine and dimethylamine ii) Aniline and N-methylaniline iii) Ethylamine and aniline

Q3. Account for the following: i) pK of aniline is more than that of methylamine. ii) Reduction of alkylcanide forms primary amine whereas alkyl isocyanide forms secondary amine.

Q4. How do you prepare the following? i) N,N-Dimethylpropanamine from ammonia ii) Propanamine from Chloroethane

Q5. Compare the basicity of the following in gaseous and in aqueous state and arrange them in increasing order of basicity. $\ce{CH3NH2, (CH3)2, NH, (CH3)3 N}$ and $\ce{NH3}$

Q6. How do you carryout the following conversions? i) N-Ethylamine to N. N-Diethyl propanamine ii) Aniline to Benzenesulphonamide

Q7. Explain with a suitable example how benzene sulphonylchloride can distinguish primary, secondary and tertiary amines.

Q8. Write the reactions of (1) aromatic and (ii) aliphatic primary amines wth nitrous acid.

Q9. Explain why amines are less acidic than alcohols of comaparable molecular masses.

Q10. How do you prepare Ethyl cyanide and Ethyl isocyanide from a common alkylhalide?

Long Answer Questions

Q1. An aromatic compound 'A' on treatment with aqueous ammonia and heating forms compound 'B' which on heating with Br, and KOH forms compound'C' of molecular formula $\ce{C6H7N}$. Write the structures and IUPAC names of compounds A,B and C.

Q2. Complete the following conversions. i. $\ce{CH3NC + HgO ?}$? (ii) $\ce{? 2H2O -> CH3NH2 + HCOOH}$ (iIi) $\ce{CH3CN + C2H5MgBr -> ?}$ (iv) $\ce{CH3CH2NH2 + CHCI3 + KOH ->}$ ? (v) NH, + 3Br,

Q3. 1) Write the structures of different isomeric amines corresponding to the molecular formula $\ce{C9H13N}$. ii) What reducing agents can bring out reduction of nitrobenzene? iii) Write the product formed when benzyl chloride is reacted with ammonia followed by treatment with methyl and ethyl chlorides

Q4. i) Identify the amide and cyanide which on reduction with appropriate reducing agent gives n-butylamine. ii) Write the mechanism of Hoffmann bromamide reaction.

Q5. How do you make the following convertions? i) Chlorophenylmethane to Phenylacetic acid ii) Chlorophenylmethane to 2-Phenylethanamine.

Q6. Identify the starting amide which gives p-methyl aniline on reaction with bromine and sodium hydroxide and write all the steps involved in the reaction.

Q7. Explain why the order of basicity for Methyl amine, N,N-dimethyl amine and N,N,N-trimethyl amine changes in gasous and aqueous medium.

Q8. Write the equations involved in the reaction of Nitrous acid with Ethylamine and aniline.

Q9. Explain with equations how methylamine, N,N-dimethylamine and N.N.N- trimethylamine react with benzenesulphonyl chloride and how this reaction is useful to separate these amines.

Q10. Explain why aniline in strong acidic medium gives a mixture of Nitro anilines and what steps need to be taken to prepare selectively p-nitoaniline.

Q11. i) Account for the stability of aromatic diazonium ions when compared to aliphatic diazonium ions.ii) Write the equations showing the conversion of aniline diazoniumchloride to a) Chlorobenzene, b) lodobenzene and c) Bromobenzene.

Q12. Complete the following conversions: Aniline to i) Fluorobenzene ii) Cyanobenzene iii) Benzene and iv) Phenol

Q13. Explain the following name reactions: i) Sandmeyer reaction ii) Gatterman reaction.

Q14. Write the steps involved in the coupling of Benzene diazonium chloride with aniline and phenol.

Q15. Write the equations involved in the conversion of acetamide and propanaldehydeoxime to methyl cyanide and ethyl cyanide respectively.