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1
6505-6508
Some of these families are manufactured for use as solvents (i e , acetone) and for preparing materials like adhesives, paints, resins, perfumes, plastics, fabrics, etc Rationalised 2023-24 229 Aldehydes, Ketones and Carboxylic Acids The common names of ketones are derived by naming two alkyl or aryl groups bonded to the carbonyl group
1
6506-6509
e , acetone) and for preparing materials like adhesives, paints, resins, perfumes, plastics, fabrics, etc Rationalised 2023-24 229 Aldehydes, Ketones and Carboxylic Acids The common names of ketones are derived by naming two alkyl or aryl groups bonded to the carbonyl group The locations of substituents are indicated by Greek letters, a a¢, b b¢ and so on beginning with the carbon atoms next to the carbonyl group, indicated as aa¢
1
6507-6510
, acetone) and for preparing materials like adhesives, paints, resins, perfumes, plastics, fabrics, etc Rationalised 2023-24 229 Aldehydes, Ketones and Carboxylic Acids The common names of ketones are derived by naming two alkyl or aryl groups bonded to the carbonyl group The locations of substituents are indicated by Greek letters, a a¢, b b¢ and so on beginning with the carbon atoms next to the carbonyl group, indicated as aa¢ Some ketones have historical common names, the simplest dimethyl ketone is called acetone
1
6508-6511
Rationalised 2023-24 229 Aldehydes, Ketones and Carboxylic Acids The common names of ketones are derived by naming two alkyl or aryl groups bonded to the carbonyl group The locations of substituents are indicated by Greek letters, a a¢, b b¢ and so on beginning with the carbon atoms next to the carbonyl group, indicated as aa¢ Some ketones have historical common names, the simplest dimethyl ketone is called acetone Alkyl phenyl ketones are usually named by adding the name of acyl group as prefix to the word phenone
1
6509-6512
The locations of substituents are indicated by Greek letters, a a¢, b b¢ and so on beginning with the carbon atoms next to the carbonyl group, indicated as aa¢ Some ketones have historical common names, the simplest dimethyl ketone is called acetone Alkyl phenyl ketones are usually named by adding the name of acyl group as prefix to the word phenone For example (b) IUPAC names The IUPAC names of open chain aliphatic aldehydes and ketones are derived from the names of the corresponding alkanes by replacing the ending –e with –al and –one respectively
1
6510-6513
Some ketones have historical common names, the simplest dimethyl ketone is called acetone Alkyl phenyl ketones are usually named by adding the name of acyl group as prefix to the word phenone For example (b) IUPAC names The IUPAC names of open chain aliphatic aldehydes and ketones are derived from the names of the corresponding alkanes by replacing the ending –e with –al and –one respectively In case of aldehydes the longest carbon chain is numbered starting from the carbon of the aldehyde group while in case of ketones the numbering begins from the end nearer to the carbonyl group
1
6511-6514
Alkyl phenyl ketones are usually named by adding the name of acyl group as prefix to the word phenone For example (b) IUPAC names The IUPAC names of open chain aliphatic aldehydes and ketones are derived from the names of the corresponding alkanes by replacing the ending –e with –al and –one respectively In case of aldehydes the longest carbon chain is numbered starting from the carbon of the aldehyde group while in case of ketones the numbering begins from the end nearer to the carbonyl group The substituents are prefixed in alphabetical order along with numerals indicating their positions in the carbon chain
1
6512-6515
For example (b) IUPAC names The IUPAC names of open chain aliphatic aldehydes and ketones are derived from the names of the corresponding alkanes by replacing the ending –e with –al and –one respectively In case of aldehydes the longest carbon chain is numbered starting from the carbon of the aldehyde group while in case of ketones the numbering begins from the end nearer to the carbonyl group The substituents are prefixed in alphabetical order along with numerals indicating their positions in the carbon chain The same applies to cyclic ketones, where the carbonyl carbon is numbered one
1
6513-6516
In case of aldehydes the longest carbon chain is numbered starting from the carbon of the aldehyde group while in case of ketones the numbering begins from the end nearer to the carbonyl group The substituents are prefixed in alphabetical order along with numerals indicating their positions in the carbon chain The same applies to cyclic ketones, where the carbonyl carbon is numbered one When the aldehyde group is attached to a ring, the suffix carbaldehyde is added after the full name of the cycloalkane
1
6514-6517
The substituents are prefixed in alphabetical order along with numerals indicating their positions in the carbon chain The same applies to cyclic ketones, where the carbonyl carbon is numbered one When the aldehyde group is attached to a ring, the suffix carbaldehyde is added after the full name of the cycloalkane The numbering of the ring carbon atoms start from the carbon atom attached to the aldehyde group
1
6515-6518
The same applies to cyclic ketones, where the carbonyl carbon is numbered one When the aldehyde group is attached to a ring, the suffix carbaldehyde is added after the full name of the cycloalkane The numbering of the ring carbon atoms start from the carbon atom attached to the aldehyde group The name of the simplest aromatic aldehyde carrying the aldehyde group on a benzene ring is benzenecarbaldehyde
1
6516-6519
When the aldehyde group is attached to a ring, the suffix carbaldehyde is added after the full name of the cycloalkane The numbering of the ring carbon atoms start from the carbon atom attached to the aldehyde group The name of the simplest aromatic aldehyde carrying the aldehyde group on a benzene ring is benzenecarbaldehyde However, the common name benzaldehyde is also accepted by IUPAC
1
6517-6520
The numbering of the ring carbon atoms start from the carbon atom attached to the aldehyde group The name of the simplest aromatic aldehyde carrying the aldehyde group on a benzene ring is benzenecarbaldehyde However, the common name benzaldehyde is also accepted by IUPAC Other aromatic aldehydes are hence named as substituted benzaldehydes
1
6518-6521
The name of the simplest aromatic aldehyde carrying the aldehyde group on a benzene ring is benzenecarbaldehyde However, the common name benzaldehyde is also accepted by IUPAC Other aromatic aldehydes are hence named as substituted benzaldehydes Rationalised 2023-24 230 Chemistry Aldehydes HCHO Formaldehyde Methanal CH3CHO Acetaldehyde Ethanal (CH3)2CHCHO Isobutyraldehyde 2-Methylpropanal g-Methylcyclohexanecarbaldehyde 3-Methylcyclohexanecarbaldehyde CH3CH(OCH3)CHO a-Methoxypropionaldehyde 2-Methoxypropanal CH3CH2CH2CH2CHO Valeraldehyde Pentanal CH2=CHCHO Acrolein Prop-2-enal Phthaldehyde Benzene-1,2-dicarbaldehyde m-Bromobenzaldehyde 3-Bromobenzaldehyde Ketones CH3COCH2CH2CH3 Methyl n-propyl ketone Pentan-2-one (CH3)2CHCOCH(CH3)2 Diisopropyl ketone 2,4-Dimethylpentan-3-one a-Methylcyclohexanone 2-Methylcyclohexanone (CH3)2C=CHCOCH3 Mesityl oxide 4-Methylpent-3-en-2-one Table 8
1
6519-6522
However, the common name benzaldehyde is also accepted by IUPAC Other aromatic aldehydes are hence named as substituted benzaldehydes Rationalised 2023-24 230 Chemistry Aldehydes HCHO Formaldehyde Methanal CH3CHO Acetaldehyde Ethanal (CH3)2CHCHO Isobutyraldehyde 2-Methylpropanal g-Methylcyclohexanecarbaldehyde 3-Methylcyclohexanecarbaldehyde CH3CH(OCH3)CHO a-Methoxypropionaldehyde 2-Methoxypropanal CH3CH2CH2CH2CHO Valeraldehyde Pentanal CH2=CHCHO Acrolein Prop-2-enal Phthaldehyde Benzene-1,2-dicarbaldehyde m-Bromobenzaldehyde 3-Bromobenzaldehyde Ketones CH3COCH2CH2CH3 Methyl n-propyl ketone Pentan-2-one (CH3)2CHCOCH(CH3)2 Diisopropyl ketone 2,4-Dimethylpentan-3-one a-Methylcyclohexanone 2-Methylcyclohexanone (CH3)2C=CHCOCH3 Mesityl oxide 4-Methylpent-3-en-2-one Table 8 1: Common and IUPAC Names of Some Aldehydes and Ketones Structure Common name IUPAC name The common and IUPAC names of some aldehydes and ketones are given in Table 8
1
6520-6523
Other aromatic aldehydes are hence named as substituted benzaldehydes Rationalised 2023-24 230 Chemistry Aldehydes HCHO Formaldehyde Methanal CH3CHO Acetaldehyde Ethanal (CH3)2CHCHO Isobutyraldehyde 2-Methylpropanal g-Methylcyclohexanecarbaldehyde 3-Methylcyclohexanecarbaldehyde CH3CH(OCH3)CHO a-Methoxypropionaldehyde 2-Methoxypropanal CH3CH2CH2CH2CHO Valeraldehyde Pentanal CH2=CHCHO Acrolein Prop-2-enal Phthaldehyde Benzene-1,2-dicarbaldehyde m-Bromobenzaldehyde 3-Bromobenzaldehyde Ketones CH3COCH2CH2CH3 Methyl n-propyl ketone Pentan-2-one (CH3)2CHCOCH(CH3)2 Diisopropyl ketone 2,4-Dimethylpentan-3-one a-Methylcyclohexanone 2-Methylcyclohexanone (CH3)2C=CHCOCH3 Mesityl oxide 4-Methylpent-3-en-2-one Table 8 1: Common and IUPAC Names of Some Aldehydes and Ketones Structure Common name IUPAC name The common and IUPAC names of some aldehydes and ketones are given in Table 8 1
1
6521-6524
Rationalised 2023-24 230 Chemistry Aldehydes HCHO Formaldehyde Methanal CH3CHO Acetaldehyde Ethanal (CH3)2CHCHO Isobutyraldehyde 2-Methylpropanal g-Methylcyclohexanecarbaldehyde 3-Methylcyclohexanecarbaldehyde CH3CH(OCH3)CHO a-Methoxypropionaldehyde 2-Methoxypropanal CH3CH2CH2CH2CHO Valeraldehyde Pentanal CH2=CHCHO Acrolein Prop-2-enal Phthaldehyde Benzene-1,2-dicarbaldehyde m-Bromobenzaldehyde 3-Bromobenzaldehyde Ketones CH3COCH2CH2CH3 Methyl n-propyl ketone Pentan-2-one (CH3)2CHCOCH(CH3)2 Diisopropyl ketone 2,4-Dimethylpentan-3-one a-Methylcyclohexanone 2-Methylcyclohexanone (CH3)2C=CHCOCH3 Mesityl oxide 4-Methylpent-3-en-2-one Table 8 1: Common and IUPAC Names of Some Aldehydes and Ketones Structure Common name IUPAC name The common and IUPAC names of some aldehydes and ketones are given in Table 8 1 or 3-Bromobenzenecarbaldehyde Rationalised 2023-24 231 Aldehydes, Ketones and Carboxylic Acids The carbonyl carbon atom is sp 2-hybridised and forms three sigma (s) bonds
1
6522-6525
1: Common and IUPAC Names of Some Aldehydes and Ketones Structure Common name IUPAC name The common and IUPAC names of some aldehydes and ketones are given in Table 8 1 or 3-Bromobenzenecarbaldehyde Rationalised 2023-24 231 Aldehydes, Ketones and Carboxylic Acids The carbonyl carbon atom is sp 2-hybridised and forms three sigma (s) bonds The fourth valence electron of carbon remains in its p-orbital and forms a p-bond with oxygen by overlap with p-orbital of an oxygen
1
6523-6526
1 or 3-Bromobenzenecarbaldehyde Rationalised 2023-24 231 Aldehydes, Ketones and Carboxylic Acids The carbonyl carbon atom is sp 2-hybridised and forms three sigma (s) bonds The fourth valence electron of carbon remains in its p-orbital and forms a p-bond with oxygen by overlap with p-orbital of an oxygen In addition, the oxygen atom also has two non bonding electron pairs
1
6524-6527
or 3-Bromobenzenecarbaldehyde Rationalised 2023-24 231 Aldehydes, Ketones and Carboxylic Acids The carbonyl carbon atom is sp 2-hybridised and forms three sigma (s) bonds The fourth valence electron of carbon remains in its p-orbital and forms a p-bond with oxygen by overlap with p-orbital of an oxygen In addition, the oxygen atom also has two non bonding electron pairs Thus, the carbonyl carbon and the three atoms attached to it lie in the same plane and the p-electron cloud is above and below this plane
1
6525-6528
The fourth valence electron of carbon remains in its p-orbital and forms a p-bond with oxygen by overlap with p-orbital of an oxygen In addition, the oxygen atom also has two non bonding electron pairs Thus, the carbonyl carbon and the three atoms attached to it lie in the same plane and the p-electron cloud is above and below this plane The bond angles are approximately 120° as expected of a trigonal coplanar structure (Figure 8
1
6526-6529
In addition, the oxygen atom also has two non bonding electron pairs Thus, the carbonyl carbon and the three atoms attached to it lie in the same plane and the p-electron cloud is above and below this plane The bond angles are approximately 120° as expected of a trigonal coplanar structure (Figure 8 1)
1
6527-6530
Thus, the carbonyl carbon and the three atoms attached to it lie in the same plane and the p-electron cloud is above and below this plane The bond angles are approximately 120° as expected of a trigonal coplanar structure (Figure 8 1) 8
1
6528-6531
The bond angles are approximately 120° as expected of a trigonal coplanar structure (Figure 8 1) 8 1
1
6529-6532
1) 8 1 2 Structure of the Carbonyl Group π Fig
1
6530-6533
8 1 2 Structure of the Carbonyl Group π Fig 8
1
6531-6534
1 2 Structure of the Carbonyl Group π Fig 8 1 Orbital diagram for the formation of carbonyl group The carbon-oxygen double bond is polarised due to higher electronegativity of oxygen relative to carbon
1
6532-6535
2 Structure of the Carbonyl Group π Fig 8 1 Orbital diagram for the formation of carbonyl group The carbon-oxygen double bond is polarised due to higher electronegativity of oxygen relative to carbon Hence, the carbonyl carbon is an electrophilic (Lewis acid), and carbonyl oxygen, a nucleophilic (Lewis base) centre
1
6533-6536
8 1 Orbital diagram for the formation of carbonyl group The carbon-oxygen double bond is polarised due to higher electronegativity of oxygen relative to carbon Hence, the carbonyl carbon is an electrophilic (Lewis acid), and carbonyl oxygen, a nucleophilic (Lewis base) centre Carbonyl compounds have substantial dipole moments and are polar than ethers
1
6534-6537
1 Orbital diagram for the formation of carbonyl group The carbon-oxygen double bond is polarised due to higher electronegativity of oxygen relative to carbon Hence, the carbonyl carbon is an electrophilic (Lewis acid), and carbonyl oxygen, a nucleophilic (Lewis base) centre Carbonyl compounds have substantial dipole moments and are polar than ethers The high polarity of the carbonyl group is explained on the basis of resonance involving a neutral (A) and a dipolar (B) structures as shown
1
6535-6538
Hence, the carbonyl carbon is an electrophilic (Lewis acid), and carbonyl oxygen, a nucleophilic (Lewis base) centre Carbonyl compounds have substantial dipole moments and are polar than ethers The high polarity of the carbonyl group is explained on the basis of resonance involving a neutral (A) and a dipolar (B) structures as shown Intext Questions Intext Questions Intext Questions Intext Questions Intext Questions 8
1
6536-6539
Carbonyl compounds have substantial dipole moments and are polar than ethers The high polarity of the carbonyl group is explained on the basis of resonance involving a neutral (A) and a dipolar (B) structures as shown Intext Questions Intext Questions Intext Questions Intext Questions Intext Questions 8 1 Write the structures of the following compounds
1
6537-6540
The high polarity of the carbonyl group is explained on the basis of resonance involving a neutral (A) and a dipolar (B) structures as shown Intext Questions Intext Questions Intext Questions Intext Questions Intext Questions 8 1 Write the structures of the following compounds (i) a-Methoxypropionaldehyde (ii) 3-Hydroxybutanal (iii) 2-Hydroxycyclopentane carbaldehyde (iv) 4-Oxopentanal (v) Di-sec
1
6538-6541
Intext Questions Intext Questions Intext Questions Intext Questions Intext Questions 8 1 Write the structures of the following compounds (i) a-Methoxypropionaldehyde (ii) 3-Hydroxybutanal (iii) 2-Hydroxycyclopentane carbaldehyde (iv) 4-Oxopentanal (v) Di-sec butyl ketone (vi) 4-Fluoroacetophenone Some important methods for the preparation of aldehydes and ketones are as follows: 1
1
6539-6542
1 Write the structures of the following compounds (i) a-Methoxypropionaldehyde (ii) 3-Hydroxybutanal (iii) 2-Hydroxycyclopentane carbaldehyde (iv) 4-Oxopentanal (v) Di-sec butyl ketone (vi) 4-Fluoroacetophenone Some important methods for the preparation of aldehydes and ketones are as follows: 1 By oxidation of alcohols Aldehydes and ketones are generally prepared by oxidation of primary and secondary alcohols, respectively (Unit 7, Class XII)
1
6540-6543
(i) a-Methoxypropionaldehyde (ii) 3-Hydroxybutanal (iii) 2-Hydroxycyclopentane carbaldehyde (iv) 4-Oxopentanal (v) Di-sec butyl ketone (vi) 4-Fluoroacetophenone Some important methods for the preparation of aldehydes and ketones are as follows: 1 By oxidation of alcohols Aldehydes and ketones are generally prepared by oxidation of primary and secondary alcohols, respectively (Unit 7, Class XII) 2
1
6541-6544
butyl ketone (vi) 4-Fluoroacetophenone Some important methods for the preparation of aldehydes and ketones are as follows: 1 By oxidation of alcohols Aldehydes and ketones are generally prepared by oxidation of primary and secondary alcohols, respectively (Unit 7, Class XII) 2 By dehydrogenation of alcohols This method is suitable for volatile alcohols and is of industrial application
1
6542-6545
By oxidation of alcohols Aldehydes and ketones are generally prepared by oxidation of primary and secondary alcohols, respectively (Unit 7, Class XII) 2 By dehydrogenation of alcohols This method is suitable for volatile alcohols and is of industrial application In this method alcohol vapours are passed over heavy metal catalysts (Ag or Cu)
1
6543-6546
2 By dehydrogenation of alcohols This method is suitable for volatile alcohols and is of industrial application In this method alcohol vapours are passed over heavy metal catalysts (Ag or Cu) Primary and secondary alcohols give aldehydes and ketones, respectively (Unit 7, Class XII)
1
6544-6547
By dehydrogenation of alcohols This method is suitable for volatile alcohols and is of industrial application In this method alcohol vapours are passed over heavy metal catalysts (Ag or Cu) Primary and secondary alcohols give aldehydes and ketones, respectively (Unit 7, Class XII) 3
1
6545-6548
In this method alcohol vapours are passed over heavy metal catalysts (Ag or Cu) Primary and secondary alcohols give aldehydes and ketones, respectively (Unit 7, Class XII) 3 From hydrocarbons (i) By ozonolysis of alkenes: As we know, ozonolysis of alkenes followed by reaction with zinc dust and water gives aldehydes, 8
1
6546-6549
Primary and secondary alcohols give aldehydes and ketones, respectively (Unit 7, Class XII) 3 From hydrocarbons (i) By ozonolysis of alkenes: As we know, ozonolysis of alkenes followed by reaction with zinc dust and water gives aldehydes, 8 2
1
6547-6550
3 From hydrocarbons (i) By ozonolysis of alkenes: As we know, ozonolysis of alkenes followed by reaction with zinc dust and water gives aldehydes, 8 2 1 Preparation of Aldehydes and Ketones 8
1
6548-6551
From hydrocarbons (i) By ozonolysis of alkenes: As we know, ozonolysis of alkenes followed by reaction with zinc dust and water gives aldehydes, 8 2 1 Preparation of Aldehydes and Ketones 8 2 8
1
6549-6552
2 1 Preparation of Aldehydes and Ketones 8 2 8 2 8
1
6550-6553
1 Preparation of Aldehydes and Ketones 8 2 8 2 8 2 8
1
6551-6554
2 8 2 8 2 8 2 8
1
6552-6555
2 8 2 8 2 8 2 Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes and Ketones and Ketones and Ketones and Ketones and Ketones Rationalised 2023-24 232 Chemistry ketones or a mixture of both depending on the substitution pattern of the alkene (Unit 9, Class XI)
1
6553-6556
2 8 2 8 2 Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes and Ketones and Ketones and Ketones and Ketones and Ketones Rationalised 2023-24 232 Chemistry ketones or a mixture of both depending on the substitution pattern of the alkene (Unit 9, Class XI) (ii) By hydration of alkynes: Addition of water to ethyne in the presence of H2SO4 and HgSO4 gives acetaldehyde
1
6554-6557
2 8 2 Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes and Ketones and Ketones and Ketones and Ketones and Ketones Rationalised 2023-24 232 Chemistry ketones or a mixture of both depending on the substitution pattern of the alkene (Unit 9, Class XI) (ii) By hydration of alkynes: Addition of water to ethyne in the presence of H2SO4 and HgSO4 gives acetaldehyde All other alkynes give ketones in this reaction (Unit 9, Class XI)
1
6555-6558
2 Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes Preparation of Aldehydes and Ketones and Ketones and Ketones and Ketones and Ketones Rationalised 2023-24 232 Chemistry ketones or a mixture of both depending on the substitution pattern of the alkene (Unit 9, Class XI) (ii) By hydration of alkynes: Addition of water to ethyne in the presence of H2SO4 and HgSO4 gives acetaldehyde All other alkynes give ketones in this reaction (Unit 9, Class XI) 1
1
6556-6559
(ii) By hydration of alkynes: Addition of water to ethyne in the presence of H2SO4 and HgSO4 gives acetaldehyde All other alkynes give ketones in this reaction (Unit 9, Class XI) 1 From acyl chloride (acid chloride) Acyl chloride (acid chloride) is hydrogenated over catalyst, palladium on barium sulphate
1
6557-6560
All other alkynes give ketones in this reaction (Unit 9, Class XI) 1 From acyl chloride (acid chloride) Acyl chloride (acid chloride) is hydrogenated over catalyst, palladium on barium sulphate This reaction is called Rosenmund reduction
1
6558-6561
1 From acyl chloride (acid chloride) Acyl chloride (acid chloride) is hydrogenated over catalyst, palladium on barium sulphate This reaction is called Rosenmund reduction 2
1
6559-6562
From acyl chloride (acid chloride) Acyl chloride (acid chloride) is hydrogenated over catalyst, palladium on barium sulphate This reaction is called Rosenmund reduction 2 From nitriles and esters Nitriles are reduced to corresponding imine with stannous chloride in the presence of hydrochloric acid, which on hydrolysis give corresponding aldehyde
1
6560-6563
This reaction is called Rosenmund reduction 2 From nitriles and esters Nitriles are reduced to corresponding imine with stannous chloride in the presence of hydrochloric acid, which on hydrolysis give corresponding aldehyde This reaction is called Stephen reaction
1
6561-6564
2 From nitriles and esters Nitriles are reduced to corresponding imine with stannous chloride in the presence of hydrochloric acid, which on hydrolysis give corresponding aldehyde This reaction is called Stephen reaction Alternatively, nitriles are selectively reduced by diisobutylaluminium hydride, (DIBAL-H) to imines followed by hydrolysis to aldehydes: 8
1
6562-6565
From nitriles and esters Nitriles are reduced to corresponding imine with stannous chloride in the presence of hydrochloric acid, which on hydrolysis give corresponding aldehyde This reaction is called Stephen reaction Alternatively, nitriles are selectively reduced by diisobutylaluminium hydride, (DIBAL-H) to imines followed by hydrolysis to aldehydes: 8 2
1
6563-6566
This reaction is called Stephen reaction Alternatively, nitriles are selectively reduced by diisobutylaluminium hydride, (DIBAL-H) to imines followed by hydrolysis to aldehydes: 8 2 2 Preparation of Aldehydes Similarly, esters are also reduced to aldehydes with DIBAL-H
1
6564-6567
Alternatively, nitriles are selectively reduced by diisobutylaluminium hydride, (DIBAL-H) to imines followed by hydrolysis to aldehydes: 8 2 2 Preparation of Aldehydes Similarly, esters are also reduced to aldehydes with DIBAL-H 3
1
6565-6568
2 2 Preparation of Aldehydes Similarly, esters are also reduced to aldehydes with DIBAL-H 3 From hydrocarbons Aromatic aldehydes (benzaldehyde and its derivatives) are prepared from aromatic hydrocarbons by the following methods: (i) By oxidation of methylbenzene Strong oxidising agents oxidise toluene and its derivatives to benzoic acids
1
6566-6569
2 Preparation of Aldehydes Similarly, esters are also reduced to aldehydes with DIBAL-H 3 From hydrocarbons Aromatic aldehydes (benzaldehyde and its derivatives) are prepared from aromatic hydrocarbons by the following methods: (i) By oxidation of methylbenzene Strong oxidising agents oxidise toluene and its derivatives to benzoic acids However, it is possible to stop the oxidation at the aldehyde stage with suitable reagents that convert the methyl group to an intermediate that is difficult to oxidise further
1
6567-6570
3 From hydrocarbons Aromatic aldehydes (benzaldehyde and its derivatives) are prepared from aromatic hydrocarbons by the following methods: (i) By oxidation of methylbenzene Strong oxidising agents oxidise toluene and its derivatives to benzoic acids However, it is possible to stop the oxidation at the aldehyde stage with suitable reagents that convert the methyl group to an intermediate that is difficult to oxidise further The following methods are used for this purpose
1
6568-6571
From hydrocarbons Aromatic aldehydes (benzaldehyde and its derivatives) are prepared from aromatic hydrocarbons by the following methods: (i) By oxidation of methylbenzene Strong oxidising agents oxidise toluene and its derivatives to benzoic acids However, it is possible to stop the oxidation at the aldehyde stage with suitable reagents that convert the methyl group to an intermediate that is difficult to oxidise further The following methods are used for this purpose (a) Use of chromyl chloride (CrO2Cl2): Chromyl chloride oxidises methyl group to a chromium complex, which on hydrolysis gives corresponding benzaldehyde
1
6569-6572
However, it is possible to stop the oxidation at the aldehyde stage with suitable reagents that convert the methyl group to an intermediate that is difficult to oxidise further The following methods are used for this purpose (a) Use of chromyl chloride (CrO2Cl2): Chromyl chloride oxidises methyl group to a chromium complex, which on hydrolysis gives corresponding benzaldehyde Rationalised 2023-24 233 Aldehydes, Ketones and Carboxylic Acids This reaction is called Etard reaction
1
6570-6573
The following methods are used for this purpose (a) Use of chromyl chloride (CrO2Cl2): Chromyl chloride oxidises methyl group to a chromium complex, which on hydrolysis gives corresponding benzaldehyde Rationalised 2023-24 233 Aldehydes, Ketones and Carboxylic Acids This reaction is called Etard reaction (b) Use of chromic oxide (CrO3): Toluene or substituted toluene is converted to benzylidene diacetate on treating with chromic oxide in acetic anhydride
1
6571-6574
(a) Use of chromyl chloride (CrO2Cl2): Chromyl chloride oxidises methyl group to a chromium complex, which on hydrolysis gives corresponding benzaldehyde Rationalised 2023-24 233 Aldehydes, Ketones and Carboxylic Acids This reaction is called Etard reaction (b) Use of chromic oxide (CrO3): Toluene or substituted toluene is converted to benzylidene diacetate on treating with chromic oxide in acetic anhydride The benzylidene diacetate can be hydrolysed to corresponding benzaldehyde with aqueous acid
1
6572-6575
Rationalised 2023-24 233 Aldehydes, Ketones and Carboxylic Acids This reaction is called Etard reaction (b) Use of chromic oxide (CrO3): Toluene or substituted toluene is converted to benzylidene diacetate on treating with chromic oxide in acetic anhydride The benzylidene diacetate can be hydrolysed to corresponding benzaldehyde with aqueous acid (iii) By Gatterman – Koch reaction When benzene or its derivative is treated with carbon monoxide and hydrogen chloride in the presence of anhydrous aluminium chloride or cuprous chloride, it gives benzaldehyde or substituted benzaldehyde
1
6573-6576
(b) Use of chromic oxide (CrO3): Toluene or substituted toluene is converted to benzylidene diacetate on treating with chromic oxide in acetic anhydride The benzylidene diacetate can be hydrolysed to corresponding benzaldehyde with aqueous acid (iii) By Gatterman – Koch reaction When benzene or its derivative is treated with carbon monoxide and hydrogen chloride in the presence of anhydrous aluminium chloride or cuprous chloride, it gives benzaldehyde or substituted benzaldehyde (ii) By side chain chlorination followed by hydrolysis Side chain chlorination of toluene gives benzal chloride, which on hydrolysis gives benzaldehyde
1
6574-6577
The benzylidene diacetate can be hydrolysed to corresponding benzaldehyde with aqueous acid (iii) By Gatterman – Koch reaction When benzene or its derivative is treated with carbon monoxide and hydrogen chloride in the presence of anhydrous aluminium chloride or cuprous chloride, it gives benzaldehyde or substituted benzaldehyde (ii) By side chain chlorination followed by hydrolysis Side chain chlorination of toluene gives benzal chloride, which on hydrolysis gives benzaldehyde This is a commercial method of manufacture of benzaldehyde
1
6575-6578
(iii) By Gatterman – Koch reaction When benzene or its derivative is treated with carbon monoxide and hydrogen chloride in the presence of anhydrous aluminium chloride or cuprous chloride, it gives benzaldehyde or substituted benzaldehyde (ii) By side chain chlorination followed by hydrolysis Side chain chlorination of toluene gives benzal chloride, which on hydrolysis gives benzaldehyde This is a commercial method of manufacture of benzaldehyde This reaction is known as Gatterman-Koch reaction
1
6576-6579
(ii) By side chain chlorination followed by hydrolysis Side chain chlorination of toluene gives benzal chloride, which on hydrolysis gives benzaldehyde This is a commercial method of manufacture of benzaldehyde This reaction is known as Gatterman-Koch reaction 1
1
6577-6580
This is a commercial method of manufacture of benzaldehyde This reaction is known as Gatterman-Koch reaction 1 From acyl chlorides Treatment of acyl chlorides with dialkylcadmium, prepared by the reaction of cadmium chloride with Grignard reagent, gives ketones
1
6578-6581
This reaction is known as Gatterman-Koch reaction 1 From acyl chlorides Treatment of acyl chlorides with dialkylcadmium, prepared by the reaction of cadmium chloride with Grignard reagent, gives ketones 8
1
6579-6582
1 From acyl chlorides Treatment of acyl chlorides with dialkylcadmium, prepared by the reaction of cadmium chloride with Grignard reagent, gives ketones 8 2
1
6580-6583
From acyl chlorides Treatment of acyl chlorides with dialkylcadmium, prepared by the reaction of cadmium chloride with Grignard reagent, gives ketones 8 2 3 Preparation of Ketones Rationalised 2023-24 234 Chemistry 2
1
6581-6584
8 2 3 Preparation of Ketones Rationalised 2023-24 234 Chemistry 2 From nitriles Treating a nitrile with Grignard reagent followed by hydrolysis yields a ketone
1
6582-6585
2 3 Preparation of Ketones Rationalised 2023-24 234 Chemistry 2 From nitriles Treating a nitrile with Grignard reagent followed by hydrolysis yields a ketone Give names of the reagents to bring about the following transformations: (i) Hexan-1-ol to hexanal (ii) Cyclohexanol to cyclohexanone (iii) p-Fluorotoluene to (iv) Ethanenitrile to ethanal p-fluorobenzaldehyde (v) Allyl alcohol to propenal (vi) But-2-ene to ethanal (i) C5H5NH+CrO3Cl-(PCC) (ii) Anhydrous CrO3 (iii) CrO3 in the presence (iv) (Diisobutyl)aluminium of acetic anhydride/ hydride (DIBAL-H) 1
1
6583-6586
3 Preparation of Ketones Rationalised 2023-24 234 Chemistry 2 From nitriles Treating a nitrile with Grignard reagent followed by hydrolysis yields a ketone Give names of the reagents to bring about the following transformations: (i) Hexan-1-ol to hexanal (ii) Cyclohexanol to cyclohexanone (iii) p-Fluorotoluene to (iv) Ethanenitrile to ethanal p-fluorobenzaldehyde (v) Allyl alcohol to propenal (vi) But-2-ene to ethanal (i) C5H5NH+CrO3Cl-(PCC) (ii) Anhydrous CrO3 (iii) CrO3 in the presence (iv) (Diisobutyl)aluminium of acetic anhydride/ hydride (DIBAL-H) 1 CrO2Cl2 2
1
6584-6587
From nitriles Treating a nitrile with Grignard reagent followed by hydrolysis yields a ketone Give names of the reagents to bring about the following transformations: (i) Hexan-1-ol to hexanal (ii) Cyclohexanol to cyclohexanone (iii) p-Fluorotoluene to (iv) Ethanenitrile to ethanal p-fluorobenzaldehyde (v) Allyl alcohol to propenal (vi) But-2-ene to ethanal (i) C5H5NH+CrO3Cl-(PCC) (ii) Anhydrous CrO3 (iii) CrO3 in the presence (iv) (Diisobutyl)aluminium of acetic anhydride/ hydride (DIBAL-H) 1 CrO2Cl2 2 HOH (v) PCC (vi) O3/H2O-Zn dust Example 8
1
6585-6588
Give names of the reagents to bring about the following transformations: (i) Hexan-1-ol to hexanal (ii) Cyclohexanol to cyclohexanone (iii) p-Fluorotoluene to (iv) Ethanenitrile to ethanal p-fluorobenzaldehyde (v) Allyl alcohol to propenal (vi) But-2-ene to ethanal (i) C5H5NH+CrO3Cl-(PCC) (ii) Anhydrous CrO3 (iii) CrO3 in the presence (iv) (Diisobutyl)aluminium of acetic anhydride/ hydride (DIBAL-H) 1 CrO2Cl2 2 HOH (v) PCC (vi) O3/H2O-Zn dust Example 8 1 Example 8
1
6586-6589
CrO2Cl2 2 HOH (v) PCC (vi) O3/H2O-Zn dust Example 8 1 Example 8 1 Example 8
1
6587-6590
HOH (v) PCC (vi) O3/H2O-Zn dust Example 8 1 Example 8 1 Example 8 1 Example 8
1
6588-6591
1 Example 8 1 Example 8 1 Example 8 1 Example 8
1
6589-6592
1 Example 8 1 Example 8 1 Example 8 1 Solution Solution Solution Solution Solution (C6H CH ) Cd + 2 CH 5 2 2 3 COCl CH3 NO2 1
1
6590-6593
1 Example 8 1 Example 8 1 Solution Solution Solution Solution Solution (C6H CH ) Cd + 2 CH 5 2 2 3 COCl CH3 NO2 1 CrO Cl 2 2 2
1
6591-6594
1 Example 8 1 Solution Solution Solution Solution Solution (C6H CH ) Cd + 2 CH 5 2 2 3 COCl CH3 NO2 1 CrO Cl 2 2 2 H3O+ (iii) C C H Hg 2+, H SO 2 4 H C 3 (iv) Intext Question Intext Question Intext Question Intext Question Intext Question 8
1
6592-6595
1 Solution Solution Solution Solution Solution (C6H CH ) Cd + 2 CH 5 2 2 3 COCl CH3 NO2 1 CrO Cl 2 2 2 H3O+ (iii) C C H Hg 2+, H SO 2 4 H C 3 (iv) Intext Question Intext Question Intext Question Intext Question Intext Question 8 2 Write the structures of products of the following reactions; (i) (ii) 3
1
6593-6596
CrO Cl 2 2 2 H3O+ (iii) C C H Hg 2+, H SO 2 4 H C 3 (iv) Intext Question Intext Question Intext Question Intext Question Intext Question 8 2 Write the structures of products of the following reactions; (i) (ii) 3 From benzene or substituted benzenes When benzene or substituted benzene is treated with acid chloride in the presence of anhydrous aluminium chloride, it affords the corresponding ketone
1
6594-6597
H3O+ (iii) C C H Hg 2+, H SO 2 4 H C 3 (iv) Intext Question Intext Question Intext Question Intext Question Intext Question 8 2 Write the structures of products of the following reactions; (i) (ii) 3 From benzene or substituted benzenes When benzene or substituted benzene is treated with acid chloride in the presence of anhydrous aluminium chloride, it affords the corresponding ketone This reaction is known as Friedel-Crafts acylation reaction
1
6595-6598
2 Write the structures of products of the following reactions; (i) (ii) 3 From benzene or substituted benzenes When benzene or substituted benzene is treated with acid chloride in the presence of anhydrous aluminium chloride, it affords the corresponding ketone This reaction is known as Friedel-Crafts acylation reaction Rationalised 2023-24 235 Aldehydes, Ketones and Carboxylic Acids The physical properties of aldehydes and ketones are described as follows
1
6596-6599
From benzene or substituted benzenes When benzene or substituted benzene is treated with acid chloride in the presence of anhydrous aluminium chloride, it affords the corresponding ketone This reaction is known as Friedel-Crafts acylation reaction Rationalised 2023-24 235 Aldehydes, Ketones and Carboxylic Acids The physical properties of aldehydes and ketones are described as follows Methanal is a gas at room temperature
1
6597-6600
This reaction is known as Friedel-Crafts acylation reaction Rationalised 2023-24 235 Aldehydes, Ketones and Carboxylic Acids The physical properties of aldehydes and ketones are described as follows Methanal is a gas at room temperature Ethanal is a volatile liquid
1
6598-6601
Rationalised 2023-24 235 Aldehydes, Ketones and Carboxylic Acids The physical properties of aldehydes and ketones are described as follows Methanal is a gas at room temperature Ethanal is a volatile liquid Other aldehydes and ketones are liquid or solid at room temperature
1
6599-6602
Methanal is a gas at room temperature Ethanal is a volatile liquid Other aldehydes and ketones are liquid or solid at room temperature The boiling points of aldehydes and ketones are higher than hydrocarbons and ethers of comparable molecular masses
1
6600-6603
Ethanal is a volatile liquid Other aldehydes and ketones are liquid or solid at room temperature The boiling points of aldehydes and ketones are higher than hydrocarbons and ethers of comparable molecular masses It is due to weak molecular association in aldehydes and ketones arising out of the dipole-dipole interactions
1
6601-6604
Other aldehydes and ketones are liquid or solid at room temperature The boiling points of aldehydes and ketones are higher than hydrocarbons and ethers of comparable molecular masses It is due to weak molecular association in aldehydes and ketones arising out of the dipole-dipole interactions Also, their boiling points are lower than those of alcohols of similar molecular masses due to absence of intermolecular hydrogen bonding
1
6602-6605
The boiling points of aldehydes and ketones are higher than hydrocarbons and ethers of comparable molecular masses It is due to weak molecular association in aldehydes and ketones arising out of the dipole-dipole interactions Also, their boiling points are lower than those of alcohols of similar molecular masses due to absence of intermolecular hydrogen bonding The following compounds of molecular masses 58 and 60 are ranked in order of increasing boiling points
1
6603-6606
It is due to weak molecular association in aldehydes and ketones arising out of the dipole-dipole interactions Also, their boiling points are lower than those of alcohols of similar molecular masses due to absence of intermolecular hydrogen bonding The following compounds of molecular masses 58 and 60 are ranked in order of increasing boiling points b
1
6604-6607
Also, their boiling points are lower than those of alcohols of similar molecular masses due to absence of intermolecular hydrogen bonding The following compounds of molecular masses 58 and 60 are ranked in order of increasing boiling points b p