Courses
Courses for Kids
Free study material
Free LIVE classes
More
JEE 2022 | Class 12

JEE Chapter - Organic Compounds Containing Nitrogen

Get interactive courses taught by top teachers
What are Organic Compounds of Nitrogen?

What are Organic Compounds of Nitrogen?


Last updated date: 25th Sep 2023
Total views: 140.1k
Views today: 14.84k

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 Chapter-wise Solutions 2022-23 


Important Topics of Organic Compound of Nitrogen

  • Aliphatic amine

  • Carbylamine reaction

  • Coupling reaction

  • Amide

  • Hoffman bromamide reaction

  • Aromatic amine

  • Nitro camide compounds

  • Nitration

  • Diazonium salt


Important Concepts of Organic Compounds Containing Nitrogen


Amine group

An amine is a functional group that has a lone pair on a nitrogen atom.

Amide group

CO-NH is the typical chemical formula for amide groups. They can be made by a reaction between an amine (NH2) and a carboxyl (CO2H) group.

Nitro group

Any of a group of chemical compounds in which the nitro group (ON=O) is incorporated into the molecular structure.

Diazonium salt

Diazonium compounds, also known as diazonium salts, are organic compounds with the functional group RN+2X, where R can be any chemical group, such as an alkyl or an aryl, and X is halogen.

Ammonolysis

Ammonolysis is a type of chemical reaction that uses ammonia as a reactant. Ammonolysis processes can be carried out with organic or inorganic substances to create amines or nitrides, respectively.


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)


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. RNH2 or ArNH2, a primary amine, is formed when one hydrogen atom of ammonia is replaced by R or Ar (1o).


If two hydrogen atoms of ammonia or one hydrogen atom of primary amine (R-NH2) are substituted by another alkyl/aryl(R') group, secondary (2o) amines are formed.


Tertiary amines (R3N) are formed when another hydrogen atom is replaced by an alkyl/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 a 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 –NH2 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)

  • 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-NH2) 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 a 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 (H2O) 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

1. 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

A nucleophile can easily cleave carbon-halogen bonds 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 (–NH2) 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 (LiAlH4) 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.


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

1. 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-NH2 + CHCl3 + 3KOH → R-NC + 3KCl + 3H2O     (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)


3. Reaction with Arylsulphonyl Chloride

Hinsberg's reagent, benzenesulphonyl chloride (C6H5SO2Cl), interacts with primary and secondary amines to produce sulphonamides.

(a) 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, it is alkali soluble.


(b) N,N-diethylbenzenesulphonamide is produced in the reaction with secondary amine.


(image will be updated soon)


Tertiary amines do not react with benzenesulfonyl 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)


At room temperature, aniline reacts with bromine water to form a white precipitate of 2,4,6-tribromoaniline. 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 addition 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 –NH2 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.


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

1. Sandmayer’s Reaction

Replacement by halide or cyanide ion: In the presence of Cu(I) 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 Iodide Ion


(image will be updated soon)


4. Replacement by Fluoride Ion


(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 –NO2 Group


(image will be updated soon)



8. Coupling Reaction


(image will be updated soon)



Solved Examples/Problems from the Chapter: Organic Compounds Containing Nitrogen

1. Complete the given reactions following the acid-base combination and name the products:

  1. CH3CH2CH2NH2 + HCl →

  2. C2H5)3N + HCl →

Ans: 


(i)


(image will be updated soon)

(ii)


(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)


a)


(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 SOCl2. 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. 


(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 is:


(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: Chromyl 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. (ii) Libermann nitrosoamine test. 


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


Conclusion

In this article, we have provided important information regarding the chapter compounds of nitrogen such as important definitions, reactions, and concepts. Students should work on more solved examples and organic compounds of nitrogen examples for securing good grades in the JEE exams.


Important Related Links for JEE Main 2022-23

See More
JEE Main Important Dates

JEE Main Important Dates

View all JEE Main Exam Dates
JEE Main 2023 January and April Session exam dates and revised schedule have been announced by the NTA. JEE Main 2023 January and April Session will now be conducted on 24-Jan-2023 to 31-Jan-2023 and 6-Apr-2023 to 12-Apr-2023, and the exam registration closes on 12-Jan-2023 and Apr-2023. You can check the complete schedule on our site. Furthermore, you can check JEE Main 2023 dates for application, admit card, exam, answer key, result, counselling, etc along with other relevant information.
See More
View all JEE Main Exam Dates
JEE Main Information

JEE Main Information

Application Form
Eligibility Criteria
Reservation Policy
Admit Card
Exam Centres
NTA has announced the JEE Main 2023 January session application form release date on the official website https://jeemain.nta.nic.in/. JEE Main 2023 January and April session Application Form is available on the official website for online registration. Besides JEE Main 2023 January and April session application form release date, learn about the application process, steps to fill the form, how to submit, exam date sheet etc online. Check our website for more details. April Session's details will be updated soon by NTA.
JEE Main 2023 applicants should be aware of the eligibility criteria before applying to the exam. NTA has released all the relevant information on the official website, i.e. https://jeemain.nta.nic.in/. JEE Main 2023 aspirants should have passed Class 12th or any other equivalent qualifying examination in 2022, 2021, or students appearing in the Class 12th final exam in 2023 can also apply. For further details, visit our website.
As per the union government’s norms, NTA has released the JEE Main 2023 January and April session reservation criteria for different candidates’ categories (SC/ST/OBC/PwD), All India Quota, State Government Quota, Deemed Universities, and more. You can check more details on Vedantu website.
NTA will release the admit card for JEE Main 2023 January and April Sessions at https://jeemain.nta.nic.in/ 15 days prior to the exam date for the registered candidates. The admit card will contain information such as the name and contact details of the candidate, the exam centre, reporting time, and examination schedule along with other important instructions for JEE Main 2023 January and April Sessions.
The NTA releases the list of JEE Main exam centres on its official website. Check JEE Main Test Centres List including states, cities here as well. We provide the complete list of JEE Main exam centres for 2023 along with the exam city & code at Vedantu. Also, check the list of documents allowed at the JEE Main exam test centres. Find all about the JEE Main 2023 exam centres, cities, location, address and code here.
It is crucial for the the engineering aspirants to know and download the JEE Main 2023 syllabus PDF for Maths, Physics and Chemistry. Check JEE Main 2023 syllabus here along with the best books and strategies to prepare for the entrance exam. Download the JEE Main 2023 syllabus consolidated as per the latest NTA guidelines from Vedantu for free.
See More
Download full syllabus
Download full syllabus
View JEE Main Syllabus in Detail
JEE Main 2023 Study Material

JEE Main 2023 Study Material

View all study material for JEE Main
JEE Main 2023 Study Materials: Strengthen your fundamentals with exhaustive JEE Main Study Materials. It covers the entire JEE Main syllabus, DPP, PYP with ample objective and subjective solved problems. Free download of JEE Main study material for Physics, Chemistry and Maths are available on our website so that students can gear up their preparation for JEE Main exam 2023 with Vedantu right on time.
See More
All
Mathematics
Physics
Chemistry
See All
JEE Main Question Papers

JEE Main Question Papers

see all
Download JEE Main Question Papers & ​Answer Keys of 2022, 2021, 2020, 2019, 2018 and 2017 PDFs. JEE Main Question Paper are provided language-wise along with their answer keys. We also offer JEE Main Sample Question Papers with Answer Keys for Physics, Chemistry and Maths solved by our expert teachers on Vedantu. Downloading the JEE Main Sample Question Papers with solutions will help the engineering aspirants to score high marks in the JEE Main examinations.
See More
JEE Main 2023 Book Solutions and PDF Download

JEE Main 2023 Book Solutions and PDF Download

View all JEE Main Important Books
In order to prepare for JEE Main 2023, candidates should know the list of important books i.e. RD Sharma Solutions, NCERT Solutions, RS Aggarwal Solutions, HC Verma books and RS Aggarwal Solutions. They will find the high quality readymade solutions of these books on Vedantu. These books will help them in order to prepare well for the JEE Main 2023 exam so that they can grab the top rank in the all India entrance exam.
See More
Maths
NCERT Book for Class 12 Maths
Physics
NCERT Book for Class 12 Physics
Chemistry
NCERT Book for Class 12 Chemistry
Physics
H. C. Verma Solutions
Maths
R. D. Sharma Solutions
Maths
R.S. Aggarwal Solutions
See All
JEE Main Mock Tests

JEE Main Mock Tests

View all mock tests
JEE Main 2023 free online mock test series for exam preparation are available on the Vedantu website for free download. Practising these mock test papers of Physics, Chemistry and Maths prepared by expert teachers at Vedantu will help you to boost your confidence to face the JEE Main 2023 examination without any worries. The JEE Main test series for Physics, Chemistry and Maths that is based on the latest syllabus of JEE Main and also the Previous Year Question Papers.
See More
JEE Main 2023 Cut-Off

JEE Main 2023 Cut-Off

JEE Main Cut Off
NTA is responsible for the release of the JEE Main 2023 January and April Session cut off score. The qualifying percentile score might remain the same for different categories. According to the latest trends, the expected cut off mark for JEE Main 2023 January and April Session is 50% for general category candidates, 45% for physically challenged candidates, and 40% for candidates from reserved categories. For the general category, JEE Main qualifying marks for 2021 ranged from 87.8992241 for general-category, while for OBC/SC/ST categories, they ranged from 68.0234447 for OBC, 46.8825338 for SC and 34.6728999 for ST category.
See More
JEE Main 2023 Results

JEE Main 2023 Results

NTA will release the JEE Main 2023 January and April sessions exam dates on the official website, i.e. {official-website}. Candidates can directly check the date sheet on the official website or https://jeemain.nta.nic.in/. JEE Main 2023 January and April sessions is expected to be held in February and May. Visit our website to keep updates of the respective important events of the national entrance exam.
See More
Rank List
Counselling
Cutoff
JEE Main 2023 state rank lists will be released by the state counselling committees for admissions to the 85% state quota and to all seats in IIT colleges. JEE Main 2023 state rank lists are based on the marks obtained in entrance exams. Candidates can check the JEE Main 2023 state rank list on the official website or on our site.
The NTA will conduct JEE Main 2023 counselling at https://josaa.nic.in/. There will be two rounds of counselling for admission under All India Quota (AIQ), deemed and central universities, NITs and CFTIs. A mop-up round of JEE Main counselling will be conducted excluding 15% AIQ seats, while the dates of JEE Main 2023 June and July session counselling for 85% state quota seats will be announced by the respective state authorities.
NTA is responsible for the release of the JEE Main 2023 June and July Session cut off score. The qualifying percentile score might remain the same for different categories. According to the latest trends, the expected cut off mark for JEE Main 2023 June and July Session is 50% for general category candidates, 45% for physically challenged candidates, and 40% for candidates from reserved categories. For the general category, JEE Main qualifying marks for 2021 ranged from 87.8992241 for general category, while for OBC/SC/ST categories, they ranged from 68.0234447 for OBC, 46.8825338 for SC and 34.6728999 for ST category.
Want to know which Engineering colleges in India accept the JEE Main 2023 scores for admission to Engineering? Find the list of Engineering colleges accepting JEE Main scores in India, compiled by Vedantu. There are 1622 Colleges that are accepting JEE Main. Also find more details on Fees, Ranking, Admission, and Placement.
See More
question-image

FAQs on JEE Chapter - Organic Compounds Containing Nitrogen

FAQ

1. What are the main points to remember while tackling problems involving Organic compounds containing nitrogen?

Students should practise writing the mechanism of different reactions to remember the concepts. Also, practising resonating structure and previous year questions will help students to score good marks.

2. Do questions from the Organic Compounds Containing Nitrogen chapter come every year in JEE Main?

yes, the Organic Compounds Containing Nitrogen chapter is one of the important chapters that comes in JEE Main every year. This chapter is considered a scoring chapter because it falls under the important topics of JEE Main examination. The important topics of this chapter are Amino acid basicity, Stability of amines, Amine preparation, and Reagents utilised.

3. What is the weightage of this chapter in JEE Main?

Nearly 1-2 questions arise in the exam from this chapter covering about 4 marks which makes about 2% of the total marks.