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1 This PDF is the Sample PDF taken from our Comprehensive Study Material for NEET & AIIMS To purchase the books, go through the link belowhttp:// ETS Comprehensive Study Material For NEET & AIIMS

2 NITRGEN AND ITS DERIVATIVES CHAPTER 13 Many years ago it was taught that plants and animals were composed of different materials: Plants, of a chemical substance of three elements- Carbon, Hydrogen and xygen; animals of one of four elements, nitrogen being added to the other three. INTRDUCTIN ''ASA GRAY'' Amines constitute an important class of organic compounds derived by replacing one or more hydrogen atoms of ammonia molecule by alkyl/aryl group(s). In nature, they occur among protein, vitamins, alkaloids and hormones. The chief commerical use of amines is as intermediates in the synthesis of medicines and fibres. Synthetic examples include polymers, dyestuffs and drugs. Two biologically active compounds, namely adrenaline and ephedrine, both containing secondary amino group, are used to increase blood pressure. Novocain, a synthetic amino compound, is used as an anaesthetic in dentistry. Benadryl, a well known antihistaminic drug also contains tertiary amino group. Quaternary ammonium salts are used as surfactants. Diazonium salts are intermediates in the preparation of a variety of aromatic compounds including dyes. In this Unit, you will learn about amines, cyanide, isocyanide and diazonium salts.

3 CHEMISTRY FR NEET & AIIMS AMINES Amines are derivatives of ammonia in which one or more hydrogen atoms are replaced by alkyl groups(s).amines are classified as primary, secondary and tertiary depanding on the number of alkyl groups attached to nitrogen atom. General formula 1 amine amine 3 amine CnHn+1 or CnHn+3 N (CnH n+1) NH (CnH n+1) 3N GENERAL METHD F PREPARATIN : (I) AMMNLYSIS F ALKYL HALIDES AND ALCHL : (a) From Ammonolysis of alkyl halides [Hofmann's ammonolysis] : When an aqueous solution of ammonia is heated with alkyl halide all the three types of amines and quaternary ammonium salt are formed. R X NH 3 HX R RX HX R NH RX HX (Quaternary ammonium salt) If ammonia is taken in excess, 1 amine is the main product. R 3 N RX RNX 4 (b) Ammonolysis of alcohols : When RH and NH 3 are passed over Al 3 or Th at 350 C all the three types of amines are formed. R H NH 3 Al / 400 C 3 R RH Al R 3 NH RH Al R 3 3 N Note : (i) Quaternary ammonium hydroxide is not formed due to steric hindrance. (ii) If excess of ammonia is used, then main product will be primary amine. (II) BY REDUCTIN : (a) With RC : RC (b) With RCN : RCN + 4H LiAlH 4 RCH or Na/CH5H Na/C H H 5 This reaction is called mendius reaction. RCH The reduction of alkyl isocynides with sodium and ethanol gives secondary amines. R NC + 4H Na/C H H 5 RNH (c) With ximes : R CH N H + 4H LiAlH 4 RCH + H Na/CH5H (d) With RN : RN + 6H Sn/HCl RNH + H In lab method we use Sn/HCl while in industrial method we use Fe / HCl. (III) BY HYDRLYSIS F : (a) R NC : Alkyl isocyanide undergoes hydrolysis with mineral acid and forms alkyl amine. R NC + H HCl R + HCH etoosindia.com India s No. 1 nline Coaching Institute

4 CHEMISTRY FR NEET & AIIMS General formula 1 amine amine 3 amine CnHn+1 or CnHn+3 N (CnH n+1) NH (CnH n+1) 3N Genral method of prepratiomn : 1. R H NH 3 Al / 400 C 3 R RH Al R 3 NH RH Al R 3 3 N. RC LiAlH 4 RCH or Na/CH5H 3. RCN + 4H Na/C H H 5 RCH 4. R Mg I + Cl R + Mg I Cl 5. C + NH + H 3 Ni CH NH + H 1 amine 6. C 6 C + Br + 4KH C 6 + K C 3 + KBr + H conc. 7. C 6 CH + N 3 H HS4 C 6 + N + C Chemical reaction : 1. R + HCl [RNH]Cl 3 High temp. R Cl + NH 3. S R NH + C S S R NH C SH HgCl R N C S + HgS + HCl 3. R + HN R H + N + H 4. H S 4 HN 3 NH 3HS 4 + +N H S 4 N 18 etoosindia.com India s No. 1 nline Coaching Institute

5 NITRGEN AND ITS DERIVATIVES Ex. 1 Amongst the following, the strongest base in aqueous medium is... (A) (B) NCCH (C) ( ) NH (D) C 6 NH Sol. (C) Compound Factors responsible for basic character are (A) Ch 3 Inductive effect (+I) (B) NC CH Inductive effect ( I) (C) ( ) NH Inductive effect (+I) and Solvation Ex. Sol. (D) N H I effect and resonance Since, +I effect and solvation increases basic character while I effect and resonance decreases basic character. Which of the following reagents would not be a good choice for reducing an aryl nitro compound to an amine (A) H (excess)/ Pt (B) LiAlH 4 in ether (C) Fe and HCl (D) Sn and HCl (B) Aryl nitro compound can t be converted into amine using LiAlH 4 in ether. H (excess)/pt SLVED EXAMPLE N Fe/HCl Sn/HCl LiAlH 4/ether No reaction Ex. 3 The source of nitrogen in Gabriel synthesis of amines is... (A) Sodium azide, NaN 3 (B) Sodium nitrite, NaN 3 (C) Potassium cyanide, KCN (D) Potassium phthalimide C 6 H 4 (C )N K + Sol. (D) Source of nitrogen in Gabriel phthalimide synthesis is potassium phthalimide C C Phthalimide H C C + RI, NK KI C N R + H /H, or H /H, CH + R 1 amine C CH Ex. 4 The best reagent for converting -phenylpropanamide into -phenylpropanamine is... (A) Excess H (B) Br in aqueous NaH (C) lodine in the presence of red phosphorus (D) LiAlH 4 in ether Sol. (D) The best reagent for converting -phenylpropanamide into -phenylpropanamine is LiAlH 4 in ether. Reaction is as given below LiAlH 4 in ether -phenyl propanamide -phenyl propanamine etoosindia.com Study with Best Etoos Faculties of Kota 19

6 CHEMISTRY FR NEET & AIIMS Exercise # 1 SINGLE BJECTIVE NEET LEVEL 1. Cyanide ion is (A) Nucleophilic (B) Electrophilic (C) Strongly acidic (D) Non-reactive and neutral. Compounds containing both amino and CH groups are known as (A) Diamines (B) Unknown (C) Amino acids (D) Enzymes 3. Which of the following is 1 amine (A) Ethylene diamine (B) Dimethyl amine (C) Trimethyl amine (D) N-methyl aniline 4. C 3 H 9 N represents (A) Primary amine (C) Tertiary amine 5. (CH ) C.CH.C.CH 3 3 (A) Diacetone (C) Diacetoneamine is (B) Secondary amine (D) All of these (B) Acetoneamine (D) Aminoacetone 6. Amides may be converted into amines by reaction named after (A) Perkin (B) Claisen (C) Hoffmann (D) Kolbe 7. Reaction C NaBr gives (A) Br (B) CH 4 (C) CBr (D) 8. Acetamide is treated separately with the following reagents. Which would give methyl amine (A) PCl 5 (B) NaH + Br (C) Sodalime (D) Hot conc. H S 4 9. The amine formed from an amide by means of bromine and alkali has (A) Same number of C atoms as that of amide (B) ne less C atom than that of amide (C) ne more C atom than that of amide (D) Two more C atoms than that of amide 10. NaCH5H CN X The compound X is (A) C (B) CH (C) C H 6 (D) NH 11. Ethylamine can be prepared by the action of bromine and caustic potash on (A) Acetamide (B) Propionamide (C) Formamide (D) Methyl cyanide 1. Ethylamine can be obtained by the (A) Action of NH 3 on ethyl iodide (B) Actio of NH 3 on ethyl alcohol (C) Both (A) and (B) (D) None of these 13. Aniline is usually purified by (A) Steam distillation (B) Simple distillation (C) Vacuum distillation (D) Extraction with a solvent 14. Reduction of nitroalkanes yields (A) Acid (B) Alcohol (C) Amine (D) Diazo compounds 15. Acetamide changes into methylamine by (A) Hofmann bromamide reaction (B) Hofmann reaction (C) Friedel-Craft s reaction (D) Hinsberg reaction 16. When methyl iodide is heated with ammonia, the product obtained is (A) Methylamine (B) Dimethylamine (C) Trimethylamine (D) A mixture of the above three amines 17. Acetanilide can be prepared from aniline and which of the following (A) Ethanol (B) Acetaldehyde (C) Acetone (D) Acetic anhydride 18. Reduction of nitroalkanes in neutral medium (e.g. Zn / NH 4 Cl) forms mainly (A) R (B) R NHH (C) R N = N Cl (D) All of these 19. Nitrosobenzene can be prepared by oxidizing aniline from (A) H S 4 (B) H S 5 (C) H S 3 (D) K Cr 7 etoosindia.com 3 India s No. 1 nline Coaching Institute

7 Exercise # 1. A secondary amine is (A) An organic compound with two groups (B) A compound with two carbon atoms and an group (C) A compound with an group on the carbon atom in number position (D) A compound in which two of the hydrogens of NH 3 have been replaced by organic groups. The structural formula of methyl aminomethane is (A) (CH 3) CH (B) (CH 3) 3 N (C) (CH 3) NH (D) CH3NH 3. Allyl isocyanide has (A) 9 sigma bonds and 4 pi bonds (B) 8 sigma bonds and 5 pi bonds (C) 8 sigma bonds, 3 pi bonds and 4 non-bonding electrons (D) 9 sigma bonds, 3 pi bonds and non-bonding electrons 4. Reduction of nitroalkanes yields (A) Acid (B) Alcohol (C) Amine (D) Diazo compounds 5. Acetamide changes into methylamine by (A) Hofmann bromamide reaction (B) Hofmann reaction (C) Friedel-Craft's reaction (D) Hinsberg reaction SINGLE BJECTIVE 6. When methyl iodide is heated with ammonia, the product obtained is (A) Methylamine (B) Dimethylamine (C) Trimethylamine (D) A mixture of the above three amines 7. Acetanilide can be prepared from aniline and which of the following (A) Ethanol (B) Acetaldehyde (C) Acetone (D) Acetic anhydride 8. Reduction of nitroalkanes in neutral medium (e.g. Zn / NH 4 Cl) forms mainly (A) R (B) R NHH (C) R N = N Cl (D) All of these 9. Nitrosobenzene can be prepared by oxidizing aniline from (A) H S 4 (B) H S 5 (C) H S 3 (D) K Cr 7 6 etoosindia.com Study with Best Etoos Faculties of Kota NITRGEN AND ITS DERIVATIVES AIIMS LEVEL 10. The Hinsberg's method is used for (A) Preparation of primary amines (B) Preparation of secondary amines (C) Preparation of tertiary amines (D) Separation of amine mixtures 11. Reaction of primary amines with aldehyde yields (A) Amides (B) Aldimines (C) Nitriles (D) Nitro compounds 1. When acetamide is treated with HN, the gas is evolved (A) H (B) (C) N (D) CH Nitrobenzene on nitration gives (A) o-dinitrobenzene (B) p-dinitrobenzene (C) m-dinitrobenzene (D) o- and p-nitrobenzene 14. Reduction of alkyl nitrites yields (A) Alcohol (B) Base (C) Amine (D) Acid 15. When primary amines are treated with HCl, the product obtained is (A) An alcohol (B) A cyanide (C) An amide (D) Ammonium salt 16. Which one is weakest base (A) Ammonia (B) Methylamine (C) Dimethylamine (D) Trimethylamine 17. Chloroform when treated with aniline and alcoholic KH gives (A) Phenyl cyanide (B) Phenyl isocyanide (C) Chlorobenzene (D) Phenol 18. Which of following do not react with HN (A) Primary nitroalkanes (B) Secondary nitroalkanes (C) Tertiary nitroalkanes (D) All of these 19. Primary amines can be distinguished from secondary and tertiary amines by reacting with (A) Chloroform and alcoholic KH (B) Methyl iodide (C) Chloroform alone (D) Zinc dust

8 CHEMISTRY FR NEET & AIIMS Exercise # 3 PART - 1 MATRIX MATCH CLUMN 1. Match each of the compunds in Column I with its characteristic reaction(s) in Column II. Column - I Column - II (A) CH CH CN (p) Reduction with Pd C/ H (B) CH C (q) Reduction with SnCl / HCl (C) CH = CH CH H (r) Development of foul smell on treatment with chloroform and alcoholic KH (D) CH CH CH (s) Reduction with diisobutylaluminium hydride (DIBAL H) (d) Alkaline hydrolysis. Match the entries in Column I with the correctly related entries in Column II. Column - I Column - II (A) H N NH Cl 3 (p) sodium fusion extract of the compound gives Prussian blue colour with FeS 4 (B) H NH I CH (q) gives positive FeCl 3 test (C) H NH Cl 3 (r) gives white precipitate with AgN 3 N NH NH3Br (D) N (s) reacts with aldehydes to form the corresponding hydrozone derivative 3. Match the entries listed in Column I with appropriate entries listed in Column II. Column - I Column - II (Amines) (Distinguish by) (A) C and C 6 (p) Carbylamine test (B) (C ) 3 N and (C ) NH (q) Azo dye test (C) C and (C ) 3 N (r) Hinsberg s reagent test (D) (C ) 3 N and C 6 (s) Liebermann nitroso reaction 30 etoosindia.com India s No. 1 nline Coaching Institute

9 NITRGEN AND ITS DERIVATIVES Exercise # 4 PART - 1 PREVIUS YEAR (NEET/AIPMT) 1. An organic compound A on reduction gives compound B which on reduction with chloroform and potassium hydroxide forms C. The compound C on catalytic reduction gives N-methylaniline. The compound A is [CBSE AIPMT 000] (A) nitrobenzene (B) nitromethane (C) methylamine (D) aniline. Intermediates formed during reaction of RC with Br and KH are[cbse AIPMT 001] (A) RCNHBr and RNC (B) RNHCBr and RNC (C) RNHBr and RCNHBr (D) RCNBr 3. CN 5. Aniline when diazotised in cold and then treated with dimethyl aniline, gives a coloured proeduct. Its structure would be [CBSE AIPMT 004] (A) CH NH N = N 3 NH (B) CH N = N 3 (C) (CH ) N N = N 3 (D) (CH ) N N = N 3 + CH3MgBr P 6. Aniline in a set of reactions yielded a product Product P in the above reaction is [CBSE AIPMT 00] H NaN A CuCN B H HCl Ni C HN D CH C (A) (B) The structure of the product D would be [CBSE AIPMT 005] CH CH (A) C 6 CH (B) C 6 CH NHCH (C) C 6 NHH (D) C 6 CH H (C) (D) 4. The final product C, obtained in this reaction Ac A Br CH B H H + Would be [CBSE AIPMT 003] NHC (A) (C) Br C (B) (D) C C Br Br 7. Electrolytic reduction of nitrobenzene in weakly acidic medium gives [CBSE AIPMT 005] (A) aniline (B) nitrosobenzene (C) N-phenyl hydroxylamine (D) p-hydroxyaniline 8. Which of the following is mroe basic than aniline? [CBSE AIPMT 006] (A) Diphenylamine (B) Triphenylamine (C) p-nitroaniline (D) Benzylamine 9. Which one of the following on reduction with LiAlH 4 yields a secondary amine?[cbse AIPMT 007] (A) Methyl isocyanide (B) Acetamide (C) Methyl cyanide (D) Nitroethane 10. Nitrobenzene on reaction with conc. HN 3 / H S 4 at C forms which one of the following products? [NEET 007] (A) 1, -dinitrobenzene (B) 1, 3-dinitrobenzene (C) 1, 4-dinitrobenzene (D) 1,, 4-trinitrobenzene 3 etoosindia.com Study with Best Etoos Faculties of Kota

10 CHEMISTRY FR NEET & AIIMS STRAIGHT BJECTIVE TYPE 1. Acetonitrile is: (A) C CN (B) CN (C) CCN (D) C 6 CH CN. In alkyl cyanide alkyl group attached with (A) C of CN group (C) Either C or N of CN group (B) N of CN group (D) Both C and N of CN group 3. Number of isomeric primary amines obtained from C 4 H 11 N are (A) 3 (B) 4 (C) 5 (D) 6 N MCK TEST 4. CuCN Product The product is CN CN (A) (B) (C) (D) 5. Ethyl amine on heating with CS in presence of HgCl forms (A) C NCS (B) (C ) S (C) (C ) CS (D) C (CS) 6. Which of the following reacts with NaN + HCl to give phenol (A) C6H5CHNH (B) (CH 3) NH (C) (D) C 6 7. When chlorobenzene is treated with NH 3 in presence of Cu in xylene at 570 K. The product obtained is (A) Benzylamine (B) Diazonium salt (C) Schiff's base (D) Aniline 8. Nitrobenzene can be prepared from benzene by using a mixture of conc. HN 3 and conc.h S 4. In the nitrating mixture, HN 3 acts as a (A) Base (B) Acid (C) Catalyst (D) Reducing agent 9. The rate determining step for the preparation of nitrobenzene from benzene is (A) Removal of 10. In this reaction N (B) Removal of N C6H5NH HCl NaN X. Product X is (A) Aniline hydrochloride (C) Benzenediazonium chloride 11. The end product of the reactions is HN PCl5 H.NH CH5NH A B C (C) Formation of (B) Nitro aniline (D) None of these N (D) Formation of (A) Ethyl cyanide (B) Ethyl amine (C) Methyl amine (D) Acetamide 1. Primary and secondary amines are distinguished by N (A) Br /KH (B) HCl 4 (C) HN (D) NH 3 etoosindia.com 39 India s No. 1 nline Coaching Institute

11 11 th Class Modules Chapter Details Physics 5 Modules Chemistry 5 Modules Mathematics 5 Modules Module-1 PHYSICS 1. Physical World & Measurements. Basic Maths & Vector 3. Kinematics Module- 1. Law of Motion & Friction. Work, Energy & Power Module-3 1. Motion of system of particles & Rigid Body. Gravitation Module-4 1. Mechanical Properties of Matter. Thermal Properties of Matter Module-5 1. scillations. Waves Module-1(PC) CHEMISTRY 1. Some Basic Conceps of Chemistry. Atomic Structure 3. Chemical Equilibrium 4. Ionic Equilibrium Module-(PC) 1. Thermodynamics & Thermochemistry. Redox Reaction 3. States f Matter (Gaseous & Liquid) Module-3(IC) 1. Periodic Table. Chemical Bonding 3. Hydrogen & Its Compounds 4. S-Block Module-4(C) 1. Nomenclature of rganic Compounds. Isomerism 3. General rganic Chemistry Module-5(C) 1. Reaction Mechanism. Hydrocarbon 3. Aromatic Hydrocarbon 4. Environmental Chemistry & Analysis f rganic Compounds Module-1 BILGY 1. Diversity in the Living World. Plant Kingdom 3. Animal Kingdom Module- 1. Morphology in Flowering Plants. Anatomy of Flowering Plants 3. Structural rganization in Animals Module-3 1. Cell: The Unit of Life. Biomolecules 3. Cell Cycle & Cell Division 4. Transport in Plants 5. Mineral Nutrition Module-4 1. Photosynthesis in Higher Plants. Respiration in Plants 3. Plant Growth and Development 4. Digestion & Absorption 5. Breathing & Exchange of Gases Module-5 1. Body Fluids & Its Circulation. Excretory Products & Their Elimination 3. Locomotion & Its Movement 4. Neural Control & Coordination 5. Chemical Coordination and Integration To purchase the books, go through the link belowhttp://

12 1 th Class Modules Chapter Details Physics 5 Modules Chemistry 5 Modules Mathematics 5 Modules Module-1 PHYSICS 1. Electrostatics. Capacitance Module- 1. Current Electricity. Magnetic Effect of Current and Magnetism Module-3 1. Electromagnetic Induction. Alternating Current Module-4 1. Geometrical ptics. Wave ptics Module-5 1. Modern Physics. Nuclear Physics 3. Solids & Semiconductor Devices 4. Electromagnetic Waves Module-1(PC) CHEMISTRY 1. Solid State. Chemical Kinetics 3. Solutions and Colligative Properties Module-(PC) 1. Electrochemistry. Surface Chemistry Module-3(IC) 1. P-Block Elements. Transition Elements (d & f block) 3. Co-ordination Compound 4. Metallurgy Module-4(C) 1. HaloAlkanes & HaloArenes. Alcohol, Phenol & Ether 3. Aldehyde, Ketone & Carboxylic Acid Module-5(C) 1. Nitrogen & Its Derivatives. Biomolecules & Polymers 3. Chemistry in Everyday Life Module-1 BILGY 1. Reproduction in rganisms. Sexual Reproduction in Flowering Plants 3. Human Reproduction 4. Reproductive Health Module- 1. Principles of Inheritance and Variation. Molecular Basis of Inheritance 3. Evolution Module-3 1. Human Health and Disease. Strategies for Enhancement in Food Production 3. Microbes in Human Welfare Module-4 1. Biotechnology: Principles and Processes. Biotechnology and Its Applications 3. rganisms and Populations Module-5 1. Ecosystem. Biodiversity and Conservation 3. Environmental Issues To purchase the books, go through the link belowhttp://

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Downloaded from Page 1 of 6 AMINES Amines are derivatives of ammonia (NH3), obtained by replacement of 1, 2 or all the 3 hydrogen atoms by alkyl and/or aryl groups. In nature amines are present in - proteins, vitamins,