ORGANIC CHEMISTRY CHEAT SHEET
[Link] TITLE MARKS
1 Haloalkenes and Haloarenes 6
2 Alcohols, phenols and Ether 6
3 Aldehydes, ketones and Carboxylic acid 8
4 Amines 6
5 Biomolecules 7
Important topics :
✓ IUPAC NAMES : All NCERT examples (1 marks)
✓ CHEMICAL TEST : Notes + NCERT Questions
8.13 Give simple chemical tests to distinguish between the following pairs of
compounds.
(i) Propanal and Propanone
(ii) Acetophenone and Benzophenone
(iii) Phenol and Benzoic acid
(iv) Benzoic acid and Ethyl benzoate
(v) Pentan-2-one and Pentan-3-one
(vi) Benzaldehyde and Acetophenone
(vii) Ethanal and Propanal
Notes for mechanisms provided in telegram channel, link in description
9.2 Give one chemical test to distinguish between the
following pairs of compounds.
(i) Methylamine and dimethylamine
(ii) Secondary and tertiary amines
(iii) Ethylamine and aniline
(iv) Aniline and benzylamine
(v) Aniline and N-methylaniline.
✓ OPTICAL ISOMERS : (2 marks)
• Important definitions – Chiral centres
- Achiral centres
- Racemization
- Mesomers etc.
*Highlighted questions number from revised class 12th NCERT book
✓ IMPORTANT MECHANISMS :
• SN1 and SN2
• Preparation of Alcohol from Alkene
• Dehydration of Ethanol to Ethene
• When 3 Methylbutan–2-ol is treated with HBr.
• Preparation of Ethanol to Ethoxethane
✓ REASONING –
9.3 Account for the following:
(i) pKb of aniline is more than that of methylamine.
(ii) Ethylamine is soluble in water whereas aniline is not.
(iii) Methylamine in water reacts with ferric chloride to precipitate
hydrated ferric oxide.
Notes for mechanisms provided in telegram channel, link in description
✓ REASONING –
9.3 Account for the following:
(iv) Although amino group is o– and p– directing in aromatic electrophilic
substitution reactions, aniline on nitration gives a substantial amount of
m-nitroaniline.
(v) Aniline does not undergo Friedel-Crafts reaction.
(vi) Diazonium salts of aromatic amines are more stable than those of
aliphatic amines.
(vii) Gabriel phthalimide synthesis is preferred for synthesising primary
amines.
7.4 Explain why propanol has higher boiling point than that of the
hydrocarbon, butane?
9.14 Give plausible explanation for each of the following:
(i) Why are amines less acidic than alcohols of comparable molecular masses?
(ii) Why do primary amines have higher boiling point than tertiary amines?
(iii) Why are aliphatic amines stronger bases than aromatic amines?
✓ INTERCONVERSIONS:
8.15 How will you bring about the following conversions in not more than
two steps?
(i) Propanone to Propene
(ii) Benzoic acid to Benzaldehyde
(iii) Ethanol to 3-Hydroxybutanal
(iv) Benzene to m-Nitroacetophenone
(v) Benzaldehyde to Benzophenone
(vi) Bromobenzene to 1-Phenylethanol
(vii) Benzaldehyde to 3-Phenylpropan-1-ol
(viii) Benazaldehyde to a-Hydroxyphenylacetic acid
(ix) Benzoic acid to m- Nitrobenzyl alcohol
8.17 Complete each synthesis by giving missing starting material, reagent or
products:
9.5 How will you convert:
(i) Ethanoic acid into methanamine
(ii) Hexanenitrile into 1-aminopentane
(iii) Methanol to ethanoic acid
(iv) Ethanamine into methanamine
(v) Ethanoic acid into propanoic acid
(vi) Methanamine into ethanamine
(vii) Nitromethane into dimethylamine
(viii) Propanoic acid into ethanoic acid?
9.8 Accomplish the following conversions:
(i) Nitrobenzene to benzoic acid
(ii) Benzene to m-bromophenol
(iii) Benzoic acid to aniline
(iv) Aniline to 2,4,6-tribromofluorobenzene
(v) Benzyl chloride to 2-phenylethanamine
(vi) Chlorobenzene to p-chloroaniline
(vii) Aniline to p-bromoaniline
(viii) Benzamide to toluene
(ix) Aniline to benzyl alcohol
9.9 Give the structures of A, B and C in the following reactions:
✓ ARRANGING:
Intext question: 6.6 Arrange each set of compounds in order of increasing boiling
points.
(i) Bromomethane, Bromoform, Chloromethane, Di-bromomethane.
(ii) 1-Chloropropane, Isopropyl chloride, 1-Chlorobutane.
Example 7.3 : Arrange the following sets of compounds in order of their
increasing boiling points:
(a) Pentan-1-ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol.
(b) Pentan-1-ol, n-butane, pentanal, ethoxyethane.
Solution:
(a) Methanol, ethanol, propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol.
(b) n-Butane, ethoxyethane, pentanal and pentan-1-ol.
Example 7.4 :
Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol, phenol, 4-
methylphenol.
Solution:
Propan-1-ol, 4-methylphenol, phenol, 3-nitrophenol, 3,5-dinitrophenol, 2,4, 6-
trinitrophenol.
Intext Question 8.3 Arrange the following compounds in increasing order of
their boiling points.
CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH3
Intext question: 8.4 Arrange the following compounds in increasing order of their
reactivity in
nucleophilic addition reactions.
(i) Ethanal, Propanal, Propanone, Butanone.
(ii) Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone
8.12 Arrange the following compounds in increasing order of their property as
indicated:
(i) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone
(reactivity towards HCN)
(ii) CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH,
CH3CH2CH2COOH (acid strength)
(iii) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid,
4-Methoxybenzoic acid (acid strength)
Example 8.2 Arrange the following compounds in the increasing order of their
boiling points:
CH3CH2CH2CHO, CH3CH2CH2CH2OH, H5C2-O-C2H5, CH3CH2CH2CH3
Ans:CH3CH2CH2CH3 < H5C2-O-C2H5< CH3CH2CH2CHO < CH3CH2CH2CH2OH
9.4 Arrange the following:
(i) In decreasing order of the pKb values:
C2H5NH2, C6H5NHCH3, (C2H5)2NH and C6H5NH2
(ii) In increasing order of basic strength:
C6H5NH2, C6H5N(CH3)2, (C2H5)2NH and CH3NH2
(iii) In increasing order of basic strength:
(a)Aniline, p-nitroaniline and p-toluidine
(b) C6H5NH2, C6H5NHCH3, C6H5CH2NH2.
(iv) In decreasing order of basic strength in gas phase:
C2H5NH2, (C2H5)2NH, (C2H5)3N and NH3
(v) In increasing order of boiling point:
C2H5OH, (CH3)2NH, C2H5NH2
(vi) In increasing order of solubility in water:
C6H5NH2, (C2H5)2NH, C2H5NH2.
✓ WORD PROBLEMS: (NCERT Examples)
Example 8.4 : An organic compound (A) with molecular formula C8H8O
forms an orange-red precipitate with 2,4-DNP reagent and gives yellow
precipitate on heating with iodine in the presence of sodium hydroxide. It
neither reduces Tollens’ or Fehlings’ reagent, nor does it decolourise bromine
water or Baeyer’s reagent. On drastic oxidation with chromic acid, it gives a
carboxylic acid (B) having molecular formula C7H6O2. Identify the compounds
(A) and (B) and explain the reactions involved.
Solutions:
(A) forms 2,4-DNP derivative. Therefore, it is an aldehyde or a ketone.
Since it does not reduce Tollens’ or Fehling reagent, (A) must be a ketone.
(A) responds to iodoform test. Therefore, it should be a methyl ketone.
The molecular formula of (A) indicates high degree of unsaturation, yet
it does not decolourise bromine water or Baeyer’s reagent. This indicates
the presence of unsaturation due to an aromatic ring.
Compound (B), being an oxidation product of a ketone should be a
carboxylic acid. The molecular formula of (B) indicates that it should
be benzoic acid and compound (A) should, therefore, be a
monosubstituted aromatic methyl ketone. The molecular formula of
(A) indicates that it should be phenyl methyl ketone (acetophenone).
Reactions are as follows:
✓ NAMED REACTIONS:
• ROSENMOUND REDUCTION • GABRIEL PTHALIMIDE REACTION
• STEPHEN REACTION • FRIEDAL CRAFT REACTION
• ETARD REACTION • COUPLING REACTION
• CLEMMENSEN REACTION • FITTIG REACTION
• WOLFF KISHNER REDUCTION • RIEMER-TIEMANN REACTION
• ALDOL REACTION • KOLBE’S REACTION
• CANNIZARO REACTION • SANDMEYER REACTION
• CROSSALDOL CONDENSATION • GATTERMANN REACTION
• HVZ REACTION • WILLIAMSON SYNTHESIS
• HOFFMANN BROMAMIDE • SWARTZ REACTION
DEGRADATION REACTION • FINKELSTEIN REACTION
• GATTERMANN KOCH REACTION • WURTZ REACTION
• CARBYLAMINE REACTION • WURTZ-FITTIG REACTION
Notes provided in telegram channel, link in description.
✓ BIOMOLECULES: Important topics
• Carbohydrates
▪ Preparation of Glucose
▪ Properties of Glucose
▪ Hydrolysis product of sucrose, lactose, maltose, amylose
• Amino Acids and Proteins
▪ Basic structure – essential and non – essential amino acids
▪ Shape of protein
▪ Secondary structure of protein
▪ Denaturation of protein
• Vitamins
• Table 10.3 from NCERT
• Nucleic acids and Hormones
▪ Difference between DNA and RNA
▪ Solved example and theory from NCERT for Hormones
