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JEE Important Chapter - Organic Compound Contains Oxygen

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Organic Compound Contains Oxygen

Organic Compound Contains Oxygen

In JEE Main Chemistry, the topic Organic Compounds containing Oxygen is very essential. Under the wide category of General Organic Chemistry, it plays a critical role. From the Organic Compounds containing Oxygen chapter, at least one or two questions are asked, totalling roughly four marks.


As a result, the total weightage of this chapter in the JEE Main exams is up to 1-2 percent. If you thoroughly understand the theoretical section of this chapter, you will have no trouble answering the chapter's questions. Ethers, Alcohols, and the Cannizzaro Reaction are a few of the concepts investigated under the Organic Compounds containing Oxygen heading.


Important Topics of Oxygen Containing Compound

  • Alcohols

  • Aldehydes

  • Ester 

  • Phenol

  • ketone

  • Acyl group

  • Ether 

  • Carboxylic acid

  • Amide 


Important Concepts of Organic Compound Contains Oxygen


Tollen’s test of aldehyde and ketone

The Tollens' test is a chemical reaction that distinguishes aldehydes from ketones because aldehydes may be oxidised to a carboxylic acid whereas ketones cannot.

Phenol 

The aromatic organic chemical phenol (also known as carbolic acid) has the molecular formula C6H5OH.

Acyl group

An acyl group is a moiety formed from an oxoacid, including inorganic acids, by removing one or more hydroxyl groups.

Alcohols

A form of an organic molecule with at least one hydroxyl functional group (OH) attached to a saturated carbon atom is known as alcohol.

Ether 

Ethers are organic compounds with an ether group, which is an oxygen atom bonded to two alkyl or aryl groups.

Carboxylic Acid

A carboxylic acid is an organic molecule in which a carbon (C) atom is double bonded to an oxygen (O) atom and a hydroxyl group (OH) is single bonded.


Oxygen Containing Organic Compounds

There are four major oxygen containing compounds in organic chemistry: A carboxylic acid is an organic molecule with a carbon (C) atom double linked to an oxygen (O) atom and a single attached hydroxyl group (OH).


Important Reactions

1. Oxymercuration-Demercuration



2.  Hydroboration Oxidation

Alkene combines with diborane to generate trialkyl boranes, which then react with alkaline H2O2 to form alcohols, resulting in anti-water Markovnikov's addition.



3. By using esters



4. Hydrolysis of alkyl halides 



Physical Properties 

The OH group has a big influence on the alcohol's characteristics.

  • The boiling points of the lower members, such as methanol, ethanol, and 1propanol, are greater.

  • Alcohols with smaller alkyl groups are more water soluble, but as the size of the alkyl group grows larger, the solubility declines.


Chemical Properties of the Alcohols

1. Reaction with Hydrogen Halides

Substitution occurs when alcohols react with a hydrogen halide, resulting in an alkyl halide and water.

 R—OH + HX → R—X + H2


2. Reaction with PX3 and PX5

Alkyl halides are formed when alcohols combine with PX3 and PX5.  

3 ROH + PBr3 → 3RBr + H3PO3

(1° or 2° alcohol)

ROH + PCl5 → RCl + POCl3 + HCl


3. Reaction with SOCl2

ROH + SOCl2 → R — Cl + SO2 + HCl


4. Esterification

The creation of an ester is the third method of replacing hydroxyl hydrogen with an acyl group. Acid chloride, acid anhydride, or carboxylic acid are all frequent sources of acyl groups (RCO). Esters form when they react with alcohol.



5. Reaction with RMgX

Alcohol is a non-acidic substance. A Grignard reagent, which is a strong base, can remove hydrogen from an alcohol's (OH) group.

CH3OH + CH3MgI → CH3OMgI + CH4


6. Reaction with Ceric Ammonium Solution

With ceric ammonium nitrate solution, an organic molecule containing one oxygen produces a red hue. Any monohydric alcohol, including phenol, can give off a red colour when it contains one oxygen. 


Methods of Preparation of Phenols

1. Hydrolysis of Chlorobenzene

Chlorobenzene is heated at 350°C under high pressure with aqueous NaOH in this procedure. The reaction creates C6H5ONa+ (sodium phenoxide), which is converted to phenol by acidification. Dow's method is the name for this reaction.



2. Alkali Fusion of Sodium Benzene Sulphonate

This process involves melting sodium benzene sulphonate with sodium hydroxide to make sodium phenoxide, which is then acidified to produce phenol.



3. Hydrolysis of Diazonium Salts

Phenol is created when a diazonium sulphate solution is steam distilled. 



4. By Distillation of Phenolic Acid

Decarboxylation occurs when phenolic acids are heated with soda lime, resulting in phenols.



Physical Properties of the Phenols

  • Phenol (C6H5OH) is a colourless solid.

  • The m.p. is 41°C. 

  • The b.p. 182°C. 

  • It becomes coloured on exposure to air. 

  • It is fairly soluble in water.


Chemical Properties of the Phenols

1. Fries Rearrangement

The ortho and para hydroxy acetophenones are produced by the Fries rearrangement of phenyl acetate with AlCl3. The ortho isomer is removed from the mixture using steam distillation.



2. Schotten  Baumann Reaction

When an alkaline phenol solution is forcefully shaken with benzoyl chloride, phenyl benzoate is produced. It's known as the Schotten Baumann response.



3. Reaction with PCl5

Aryl chloride is generated when phenol is treated with PCl5 (poor yield). Triphenyl phosphate is the major product of this process. 



4. Reaction with NH3

When phenol is treated with ammonia at 300°C under high pressure in the presence of anhydrous AlCl3, ZnCl2, or CaCl2, aniline is produced. 



5. Reaction with Zn dust

When phenols are heated with Zn dust, aromatic hydrocarbons are formed.



6. Kolbe's Schmidt Reaction

When carbon dioxide gas is passed through sodium phenoxide at 400 degrees Celsius and 67 pounds per square inch of air pressure, sodium salicylate is created, which when acidified yields salicylic acid, but some para isomer is also produced.



7. Reimer Tiemann Reaction





Methods of Preparation of Ethers

1. Williamson's Continuous Etherification Process

2ROH + 2Na → 2RO-Na+ + H2

RO-Na+ + R’X → R-O-R’ + NaX

It involves sodium alkoxide reacting with an alkyl halide. The action of Na on alcohol produces sodium alkoxide.


2. Intermolecular Dehydration of Alcohols 

ROH + HOR → R-O-R + H2O      (at 140 degrees celsius temperature)


Physical Properties of the Ethers

  • Ethers boil at a substantially lower temperature than the alcohols from which they are formed or similar molecular weight alcohols.

  • The boiling points are very similar to those of similar molecular complexity substituted alkanes.


Chemical Properties of the Ethers

1. Salt formation

Though ethers are neutral compounds, these form oxonium salts with inorganic acids.



This reaction is due to lone pairs of electrons on oxygen of the ether functional group.


2. Cleavage by Acids

R-O-R + HX → RX + R’OH + R’X + H2O

Reactivity of HX : HI > HBr > HCl

Cleavage takes place only under vigorous conditions, i.e., concentrated acids (usually HI or HBr) and at high temperatures.

Action of HI

(a) At room temperature



(b) At 100° C (excess of HI) 



Thus, the metameric ethers can be easily identified by the cleavage with HI.


3. Action of PCl5 or SOCl2



Thus, the reaction of PCl5 or SOCl2 can be used to identify the metameric ethers.


Aldehydes & Ketones

Aldehydes and ketones belong to a class of compounds having general formula CnH2nO and are represented as RCHO and RR'CO, respectively.


Methods of Preparation of Aldehydes

1. Oxidation of primary alcohols

Oxidation can be affected with acidic K2Cr2O7 or with PCC (Pyridine Chlorochromate, mild oxidising agent) in CH2Cl2.



2. Oxidation of Methylbenzenes



3. By Heating a Mixture of the Calcium Salts of Formic Acid and any one of its Homologues



Methods of Preparation of Ketones

1. Oxidation of Secondary Alcohols



2. By Heating the Calcium Salt of any Monocarboxylic Acid other than Formic Acid



3. Friedel – Crafts Acylation

Used for the preparation of aliphatic aromatic ketones or aromatic ketones.



Physical Properties of Aldehydes and Ketones

The polar carbonyl group makes aldehydes and ketones polar compounds and hence they have higher boiling points than non-polar compounds of comparable molecular weights.


Chemical Properties of Aldehydes and Ketones

1. Oxidation

(a)


(b) Tollen's Reagent

 A specific oxidant for RCHO is Ag(NH3)2+. Ketones do not give this reaction.



(c) Strong Oxidants

Ketones resist mild oxidation, but with strong oxidants at high temperature, they undergo cleavage of C-C bond on either side of the carbonyl group.




(d) Haloform Reaction is shown by methyl ketones.

CH3COR are readily oxidised by NaOI (NaOH + I2) to iodoform, CHI3, and RCO2Na.



2. Reduction

(a) Reduction to alcohols

Reduction to alcohols can be achieved either by hydrogenation in the presence of Pt or Pd or by LiAlH4/NaBH4.



(b) Reduction to Hydrocarbons



3. Addition Reactions of Nucleophiles

The carbon of the carbonyl group is electrophilic and thus initially attacked by a nucleophile.



(a) Addition of Grignard Reagent 



(b) Addition of Hydrogen Cyanide



(c) Addition of Sodium Bisulfite

Bisulfite compound formation is confined to aldehydes, methyl ketones, and some cyclic ketones.



(d) Nucleophilic Addition of Derivatives of Ammonia



4. Addition of Alcohols

The carbonyl compounds react with alcohols, R'OH, to yield hemiacetals.



5. Cannizzaro Reaction



6. Aldol Condensation



7. Perkin Condensation



8. Beckmann Rearrangement

The acid catalysed conversion of ketoximes to N substituted amides is known as Beckmann rearrangement.



Methods of Preparation of Carboxylic Acids

1. By Oxidation of Primary Alcohol



2. By Hydrolysis of Cyanides



General Physical Properties of the Carboxylic Acids

  • The molecules of carboxylic acids are polar and exhibit hydrogen bonding. 

  • The first four members are miscible with water. The higher acids are virtually insoluble. The simplest aromatic acid, benzoic acid, contains too many carbon atoms to show appreciable solubility in water.


General Chemical Properties of the Carboxylic Acids

  • The carboxylic acids react with metal to liberate hydrogen and are soluble in NaOH and NaHCO3 solutions. 

  • Carboxylic acid reacts with halogenated compounds and forms acid halide.



  • Carboxylic acid gets reduced to alcohols.



  • Hell Volhard Zelinsky Reaction: Aliphatic carboxylic acids react with Br2 or Cl2 in presence of phosphorus (or phosphorus halides) to give haloacids.



  • Schmidt Reaction: Carboxylic acids react with hydrazoic acid in presence of concentrated H2SO4 to give amine.

  • Benzoic acid is attacked by the usual electrophilic reagents Chlorine, Bromine, Nitric and sulphuric acids to give m-derivatives.



Derivatives of Carboxylic Acids

Acid derivatives are the compounds in which OH group of carboxyl group has been replaced by Cl, COR, NH2, or OR'.



Reactions of Acyl Chloride



Reactions of Carboxylic Acid Anhydrides



Preparation of Esters

1. Esters from Acyl Chlorides




2. From ketones (Baeyer-Villiger Oxidation)



Reactions of Esters

1. Base Promoted Hydrolysis of Esters: Saponification

The carboxylate ion is very unreactive towards nucleophilic substitution because it is negatively charged, hence the reaction is essentially irreversible.



2. Reaction with Grignard Reagent



Preparation of Acid Amides

1. By Heating Ammonium Carboxylate

RCOONH4 → RCONH2 + H2O       (on heating)


Reactions of Acid Amides

1. Hydrolysis



2. Hoffmann’s Bromamide Reaction

Amides (having a primary nitrogen atom) react with bromine in the presence of alkali to form a primary amine having one carbon atom less than the parent amide.



Solved Examples/Problems from the Chapter: Organic Compound Containing Oxygen

1. Give the structures and IUPAC names of the products expected from the given reaction: catalytic reduction of butanal.

Solution: The catalytic reduction of butanal takes in the presence of a reducing agent. This reaction of butanal will lead to the formation of butanol. 



Key Points: Aldehyde is reduced to give alcohols.


2. Write structures of the products of the given reaction.



Solution: The product formed in the above reaction will be 2-Methylbutanol. The structure of this compound is given below.



Key Points: Aldehyde group is reduced to alcohols. The chain with which the functional group is attached is considered as the parent chain. 


Solved Problems of Previous Year Question from the Organic Compound Contains Oxygen

1.



Options:

(a)


(b)


(c)




(d)




Ans: The correct answer is option b. 



Trick: The given reaction is dependent on the formation of stable carbocation. 


2. Predominant product is



Options:

(a)


(b)



(c)


(d)


Ans: The correct answer is option b.



Trick: OH group is activating in nature. So, NO2 will attack at ortho and para position, but para position is already blocked; therefore, NO2 is only attached at ortho position w.r.t. OH group.


3. The structure of the starting compound P used in the reaction given below is:


































Ans: The correct answer is option B.




Trick: The given reaction is chloroform (CHCl3) reaction. 


Practice Questions

1. Arrange the sets of compounds in order of their increasing boiling points:

Pentan-1-ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol 

Ans: Methanol, ethanol, propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol.


2. What will be the product formed in dinitration of 3-methylphenol?

Ans:



Conclusion

In this article, we have provided important information regarding the chapter Organic Compounds Containing Oxygen such as important concepts, reactions, etc. Students should work on more solved examples and previous year question papers for securing good grades in the JEE Main exams. 

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JEE Main 2022 Book Solutions and PDF Download

JEE Main 2022 Book Solutions and PDF Download

View all JEE Main Important Books
In order to prepare for JEE Main 2022, 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 2022 exam so that they can grab the top rank in the all India entrance exam.
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books
Maths
NCERT Book for Class 12 Maths
books
Physics
NCERT Book for Class 12 Physics
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JEE Main Mock Tests

JEE Main Mock Tests

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JEE Main 2022 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 2022 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.
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JEE MAIN MOCK TEST - 1
3 hr  • 75 questions • OBJECTIVE
JEE MAIN MOCK TEST - 3
3 hr  • 75 questions • OBJECTIVE
JEE MAIN MOCK TEST - 2
3 hr  • 75 questions • OBJECTIVE
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JEE Main 2022 Cut-Off

JEE Main 2022 Cut-Off

JEE Main Cut Off
NTA is responsible for the release of the JEE Main 2022 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 2022 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.
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JEE Main 2022 Results

JEE Main 2022 Results

JEE Main 2022 June and July Session Result - NTA has announced JEE Main result on their website. To download the Scorecard for JEE Main 2022 June and July Session, visit the official website of JEE Main NTA.
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Rank List
Counselling
Cutoff
JEE Main 2022 state rank lists will be released by the state counselling committees for admissions to the 85% state quota and to all seats in NITs and CFTIs colleges. JEE Main 2022 state rank lists are based on the marks obtained in entrance exams. Candidates can check the JEE Main 2022 state rank list on the official website or on our site.
The NTA will conduct JEE Main 2022 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 2022 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 2022 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 2022 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 2022 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.
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FAQs on JEE Important Chapter - Organic Compound Contains Oxygen

FAQ

1. In the JEE Main examination, how important is the alcohol chapter?

Nearly 1-2 questions arise in the exam from this chapter covering about 8 marks which makes about 2% of the total marks.

2. What are the main points to remember while tackling problems involving halogen-containing organic compounds?

Students should practise writing the mechanism of the reaction for solving the questions from the JEE Main Chemistry Organic Compounds Containing Halogens.

3. Are previous year question papers enough for scoring good marks in JEE Main?

NCERT and previous year JEE Main papers are adequate to score good marks (200+) in JEE Main. Solving previous 10-year IIT-JEE exams gives us a significant edge because 3-4 questions with the same answers are sure to be repeated every year.