Vedaniti, Lear UNE Online Organic Compounds Containing Nitrogen Chapter - Chemistry JEE Main Concepts of Organic Compounds Containing Nitrogen for JEE Main Chemistry In the atmosphere, a wide range of nitrogenous compounds has been found. Some of the organic compounds of nitrogen are Amines, amides, alkyl nitrates, nitrosamines, nitroarenes, and peroxyacyl nitrates. Amphetamines, amides, and nitro compounds are among the most crucial topics that must be covered in order to pass entrance exams. In this article, we'll go over all of the main aspects of amine, amide, and nitro compounds. JEE Main Chemistry Chapters 2024Vedaniti, Lear NEOnlne ae A Tey 4 |Some Basic Concepts in 2 Blooe Elements Chemistry 2 | States of Matter D—and F — Block Elements 3 Atomic Structure Co-ordination Compounds Chemical Bonding and 4 iMeleciler Sinica Environmental Chemistry 5 Caan gnennadaaies Purification and Characterisation of Organic Compounds 6 | Solutions Goneral Organic Chemistry 7 | Equilibrium Hydrocarbons _ | Redox Reactions and Organic Compounds Containing Electrochemistry Halogens «| chemical kinetics Organic Compounds Containing Oxygen ra Organic Compounds Containing Nitrogen “4 Classification Elements Dohme Periodicity Properties » General Principles and 12 | Processes of Isolation of Biomolecules Metals: 13 | Hydrogen Chemistry in Everyday Life 14 S* Block Elements 28 Principles Related to Practical Chemistry Important Topics of Organic Compound of Nitrogen ChapterVedaniti, Lear UNE Online * Aliphatic amine * Carbylamine reaction + Coupling reaction + Amide * Hoffman bromamide reaction * Aromatic amine + Nitro camide compounds * Nitration + Diazonium salt Organic Compounds Containing Nitrogen Important Concept for JEE MainVedaniti, Lear NEOnlne An amine is a functional group that Amine grou oom has alone pair on a nitrogen atom CO-NH is the typical chemical formula for amide groups. They can be made Amide group by a reaction between an amine (NH;) and a carboxyl (CO,H) group. Any of a group of chemical fh Nitro group compounds in which the nitro group (ON=0) is incorporated into the molecular structure Diazonium compounds, also known as diazonium salts, are_-—_ organic. compounds with the functional group RN*.X, where R can be any chemical group, such as an alkyl or an aryl, and Xis halogen Diazonium salt Ammonolysis is a type of chomical reaction that uses ammonia as a reactant. Ammonolysis processes can be carried out with organic or inorganic substances to create amines or nitrides, respectively. Ammonolysis. What are Amines? Amines are ammonia derivatives that are made by replacing one, two, or all three hydrogen atoms with alkyl and/or aryl groups. Structure of Amine (image will be updated soon)Vedaniti, Lear UNE Online Classification of Nitrogenous Compounds (Amine) Number of hydrogen atoms in ammonia molecules that are replaced by alkyl or aryl groups decide the class of amines. RNH, or ArNH,, a primary amine, is formed when one hydrogen atom of ammonia is replaced by R or Ar (1°) If two hydrogen atoms of ammonia or one hydrogen atom of primary amine (R-NH,) are substituted by another alkyV/aryl(R’) group, secondary (2°) amines are formed. Tertiary amines (R,N) are formed when another hydrogen atom is replaced by an alkyV/aryl group Nomenclature of Amines An aliphatic amine is named in the common system by prefixing the alkyl group to amine. resulting in alkylamine as @ single word (e.g., methylamine). When two or more groups in a secondary or tertiary amine are the same, the prefix di or tri is added before the name of the alkyl group. Alkanamines are the names given to amines in the IUPAC system If more than one amino group is present at different places in the parent chain, their positions are indicated by assigning numbers to the carbon atoms bearing -NH, groups and attaching a suitable prefix to the amine such as di, tri, etc. The letter ‘e' from the hydrocarbon part's suffix is kept Properties of Organic Compounds Containing Nitrogen (Amines)Vedaniti, Lear UNE Online + Lower (amines with less carbon) aliphatic amines exist in gaseous state with a fishy odour. * Aniline and other arylamines are generally colourless, but due to air oxidation, they become coloured with storage * Because they can establish hydrogen bonds with water molecules, lower aliphatic amines are soluble in water. However, when the molecular mass of amines (R-NH,) increases, solubility declines due to the increased size of the hydrophobic alkyl component + Because of hydrogen bonding between the nitrogen of one molecule and the hydrogen of another, primary and secondary amines form intermolecular associations. Because primary amines have two hydrogen atoms available for hydrogen bond formation, they have higher intermolecular interaction than secondary amines. Because there is no hydrogen atom available for hydrogen bond formation, tertiary amines do not exhibit intermolecular interaction. As @ result, the boiling temperatures of isomeric amines are in the following order: Primary > Secondary > Tertiary. + Benzenediazonium chloride is a crystalline substance that is colourless. It is generally water (H,0) soluble and generally stable at room temperature, but when warmed, it reacts with water In the dry state, it decomposes quickly. Water insoluble, benzenediazonium fluoroborate is stable at ambient temperature + Amines are reactive because of the difference in electronegativity between nitrogen and hydrogen atoms, as well as the presence of an unshared pair of electrons above the nitrogen atom Preparation Reaction for Amines 4. Reduction of Nitro Compounds By passing hydrogen gas through finely divided nickel, palladium, or platinum, nitro compounds are reduced to amines, as well as by reduction with metals in an acidic media. (image will be updated soon) 2. Ammonolysis of Alkyl HalideVedaniti, Lear UNE Online A nucleophile can easily cleave carbon-halogen bands in alkyl or benzyl halides. As a result, when an alkyl or benzyl halide reacts with an ethanolic solution of ammonia, the halogen atom is replaced by an amino (-NH.) group in a nucleophilic substitution reaction. (image will be updated soon) (image will be updated soon) ‘Treatment with a strong base yields the free amine from the ammonium salt: (image will be updated soon) 3. Reduction of Nitriles Primary amines are formed when nitriles are reduced with lithium aluminium hydride (LIAIH4) or hydrogenated catalytically. (image will be updated soon) 4. Reduction of Amides ‘When amides are reduced with lithium aluminium hydride, amines are formed (image will be updated soon) 5. Gabriel Phthalimide Reaction Primary amines are made via the Gabriel synthesis method. When phthalimide is treated with ethanolic potassium hydroxide, it generates a potassium salt, which when heated with an alkyl halide and then alkaline hydrolyzed yields the primary amine.Vedaniti, Lear UNE Online Because aryl halides do not undergo nucleophilic substitution with the anion generated by phthalimide, this approach cannot be used to make aromatic primary amines. (image will be updated soon) 6. Hoffmann Bromamide Degradation Reaction By treating an amide with bromine in an aqueous or ethanolic solution of sodium hydroxide, Hoffmann created a method for preparing primary amines (image will be updated soon) Chemical Reactions of Amine 4. Carbylamine Reaction When primary amines are heated with chloroform and ethanolic potassium hydroxide, they generate isocyanides or carbylamines, which have a horrible odour. This reaction does not occur in secondary or tertiary amines. R-NH, + CHCI, + 3KOH — R-NC + 3KCI+3H,O (on heating) 2. Reaction with Nitrous Acid When primary aliphatic amines react with nitrous acid, they produce aliphatic diazonium salts, which are unstable and release nitrogen gas and alcohols in large quantities. (image will be updated soon) At low temperatures (273-278 K), aromatic amines react with nitrous acid to create diazonium ions. (image will be updated soon)Vedaniti, Lear NEOnlne 3. Reaction with Arylsulphony! Chloride Hinsberg’s reagent, benzenesulphonyl chloride (C,H,SO,Cl), interacts with primary and secondary amines to produce sulphonamides. (@) N-ethylbenzenesulphonyl amide is formed by reacting benzenesulphonyl chloride with primary amine. (image will be updated soon) Due to the presence of a strong electron withdrawing sulfonyl group, the hydrogen linked to nitrogen in sulphonamide is extremely acidic. As a result, itis alkali soluble (b) N,N-diethylbenzenesulphonamide is produced in the reaction with secondary amino (image will be updated soon) Tertiary amines do not react with benzenesulfony| chloride. 4. Electrophilic Substitution Reaction An ortho-para directing group is the Amine group. It is subjected to a number of electrophilic substitution processes a. Bromination: (image will be updated soon)Vedaniti, Lear UNE Online At room temperature, aniline reacts with bromine water to form a white precipitate of 2,4,6- triromoaniline. In the presence of an acetyl group, controlled bromination can occur. It shields the amine group and keeps uncontrolled halogenation under control (bromination), (image will be updated soon) (b) Nitration Aniline is protonated to create the meta directing anilinium ion in a very acidic solution. As a result, in adcition to ortho and para derivatives, a considerable number of meta derivatives are generated (image will be updated soon) The nitration reaction can be regulated and the p-nitro derivative obtained as the primary product by protecting the -NH, group via an acetylation reaction with acetic anhydride (image will be updated soon) (C) Sulphonation Aniline combines with concentrated sulphuric acid to make anilinium hydrogensulphate, which produces p-aminobenzene sulphonic acid when heated with sulphuric acid at 453-473K. (image will be updated soon) Why Aniline do not Undergo Friedel Crafts Reaction Because the Lewis acid, aluminium chloride, is utilised as a catalyst, aniline does not undergo Friedel-Crafts reaction (alkylation and acetylation). As a result, the nitrogen in aniline gains a positive charge, acting as a powerful deactivate group for subsequent reactionsVedaniti, Lear UNE Orne Resonance in Diazonium Salt (image will be updated soon) Preparation Method of Diazonium Salt The reaction of aniline with nitrous acid at 273-278K produces benzenediazonium chloride. The reaction of sodium nitrite with hydrochloric acid produces nitrous acid in the reaction mixture. Diazotization is the process of converting primary aromatic amines into diazonium ions. (image will be updated soon) Reactions of Diazonium Salt 4. Sandmayer's Reaction Replacement by halide or cyanide ion: In the presence of Cu(|) ions, the nucleophiles Cl-, Br-, and CN- can easily be introduced into the benzene ring. The Sandmeyer reaction is the name for this reaction (image will be updated soon) 2. Gatterman Reaction By treating the diazonium salt solution with the appropriate halogen acid in the presence of copper powder, chlorine or bromine can be introduced into the benzene ring. The Gatterman reaction is the name for this (image will be updated soon) 3. Replacement by lodide lonVedaniti, Lear UNE Online (image will be updated soon) 4. Replacement by Fluoride lon (image will be updated soon) 5. Replacement by H (image will be updated soon) 6. Replacement by Hydroxyl Group (image will be updated soon) 7. Replacement by -NO, Group (image will be updated soon) 8. Coupling Reaction (image will be updated soon) Diazonium Salts: Importance in Synthetic Organic Chemistry Diazonium salts are a class of organic compounds that contain the diazonium functional group (N2+). They are highly significant in synthetic organic chemistry for several reasons, making them a crucial topic for JEE Main students to understand. Here, we delve into their importanceVedaniti, Lear UNE Online + Azo Dye Synthesis: Diazonium salts are pivotal in the synthesis of azo dyes, which are widely used in the textile industry for coloring fabrics. This process involves the reaction of a diazonium salt with an aromatic amine, resulting in the formation of colorful azo compounds. + Reagent in the Sandmeyer Reaction: Diazonium salts are used in the Sandmeyer reaction to introduce various functional groups into arometic compounds. For example they can be used to replace the -N2+* group with other groups like -Cl, -Br, -F, -OH, or - CN, leading to the synthesis of a wide range of organic compounds. * Preparation of Aryl Halides: 8y reacting diazonium salts with cuprous salts, aryl halides can be synthesized. These aryl halides are versatile intermediates for a multitude of organic reactions + Phenol Synthesis: Diazonium salts can be used to synthesize phenols by treating them with water or aqueous mineral acids. This reaction is significant for the preparation of various phenolic compounds. * Carboxylic Acid Synthesis: Diazonium salts can be converted into carboxylic acids. The replacement of -N2+ with -COOH Is a valuable transformation in organic synthesis. + Energetic Materials: Certain diazonium salts are used in the production of energetic materials, including explosives and propellants. This application highlights their significance in various industries + Pharmaceuticals and Agrochemicals: Diazonium salts play a role in the synthesis of many pharmaceutical and agrochemical compounds, contributing to the development of essential products that improve health and agriculture + Flavor and Fragrance Industry: Azo compounds derived from diazonium salts are used in the flavor and fragrance industry to create a wide array of aromatic compounds JEE Main Organic Compounds Containing Nitrogen Solved Examples 4. Complete the given reactions following the acid-base combination and name the products: i. CH,CH,CH,NH, + HCI > I. CH),N + HCI > Ans:Vedaniti, Lear UNE Online a (image will be updated soon) (i) (image will be updated soon) Key point: It is a general acid base reaction in which an amine group of primary amine and secondary amine accepts a proton by forming salt and behaves like a base. 2.Write down the chemical reaction between aniline and benzoyl chloride, as well as the name of the resulting product. Ans: (image will be updated soon) Key Point: This reaction is an acetylation reaction, which is used to protect the amine group from uncontrolled substitution of the electrophile in the electrophilic substitution reaction Solved Problems of Previous Year Question from the Chapter: Organic Compounds Containing Nitrogen 1. The major product formed in the following reaction is: (image will be updated soon)Vedaniti, Lear UNE Online (image will be updated soon) b) (image will be updated soon) c) (image will be updated soon) d) (image will be updated soon) Ans: The correct answer is option 3. Only primary amines react with hinsberg reagents and forms precipitate that dissolves in addition to alkali (image will be updated soon) Trick: Acylation takes place in the presence of SOCI,. Acyl group in the presence of alcohol produces esters. 2. The major product of the following reaction is: (image will be updated soon) (image will be updated soon) Ans: The correct answer is option c.Vedaniti, Lear UNE Online (image will be updated soon) Trick: This reaction will follow hoffmann’s bromamide degradation reaction. The aliphatic diazonium salt is not stable, it gets converted into an alcohol 3. In the following sequence of the reaction, the final product D i: (image will be updated soon) (image will be updated soon) Ans: The correct answer is option c (image will be updated soon) (image will be updated soon) (image will be updated soon) Trick: Chromy| chloride is an oxidising agent and hydrogen in the presence of palladium is a reducing agent. Secondary alcohol is oxidised to form ketone Practice Questions 1. To discriminate between the following pairs of substances, perform one chemical test. (i) Methylamine and dimethylamine (ii) Secondary and tertiary amines Ans: (i) Carbylamine test. (ji) Libermann nitrosoamine testVedaniti, Lear UNE Online 2. Describe a method for determining which amines are primary, secondary, and tertiary. Also, write down the chemical equations for the reactions. Ans: Hinsberg's test JEE Main Chemistry Organic Compounds Containing Nitrogen Study Materials Here, you'll find 2 comprehensive collection of study resources for Organic Compounds Containing Nitrogen designed to help you excel in your JEE Main preparation. 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Explore the links below to enrich your Chemistry preparationVedaniti, Lear NEOnlne BUS SECIS mel CEU ge Ca LCC JEE Main Chemistry Previous Year Question Papers JEE Main Chemistry Mock Test JEE Main Chemistry Formula JEE Main Sample Paper JEE Main Chemistry Difference Between Conclusion The JEE Main chapter on "Organic Compounds Containing Nitrogen" is a foundational and integral part of organic chemistry. This chapter equips students with a comprehensive understanding of the diverse and vital compounds that contain nitrogen functionalities. Knowledge of this chapter is essential for grasping the complex structures, nomenclature, reactions, and applications of these compounds. It forms the basis for advanced studies in organic chemistry, enabling students to explore the intricate world of organic synthesis and mechanisms. Mestery of this chapter empowers JEE Main students to tackle challenging organic reactions, synthesize valuable compounds, and contribute to the fields of pharmaceuticals, chemicals, and materials science.Lear UNE Online Hi SKTV, Best courses for you Crash course One-to-one LIVE Books classes Starting from &8,000 ‘Starting trom 1,800/nr Starting from &3,330 Test series Starting from 23,880 Show more courses LIVE MasterclassLIVE 55) 1 EERE ESErso E Chemisty Dropper Special: Markonioff's rule Graphs of Kinematics using Grade 9 fea Noreen eon em a RCs Ree eee TNA cue RRR ey Book a Free Session Now