Organic Chemistry Revision Series for JEE, NEET, Class 11 and 12

General Organic Chemistry

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Mindmap

Acidic and Basic Strength

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Mindmap

Hydrocarbons

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Mindmap

Optical Isomerism

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Mindmap

Haloalkanes and Haloarenes

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Mindmap

Alcohols, Phenols and Ethers

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Mindmap

Carbonyl Compounds

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Mindmap

Aldol, Cannizzaro and Haloform Reactions

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Mindmap

Name Reactions

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Mindmap

Oxidation Reactions

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Mindmap

Reduction Reactions

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Mindmap

Carboxylic Acids

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Mindmap

Nitrogen-Containing Compounds

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Mindmap

Biomolecules

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Mindmap

Polymers

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Mindmap

Chemistry in Everyday Life

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Mindmap

Atomic Structure (foundation)

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Mindmap

Chemical Bonding (foundation)

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Mindmap

Periodic Table (foundation)

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Mindmap

General Organic Chemistry

Stability of carbocations $3^\circ > 2^\circ > 1^\circ > \mathrm{CH_3^+}$, and of free radicals in the same order. Allylic and benzylic species are more stable. Electronic effects: inductive, resonance, hyperconjugation.

Acidic and basic strength

Acid strength: carboxylic acids > phenols > alcohols. In water, the basicity of the methylamines is $(\mathrm{CH_3})_2\mathrm{NH} > \mathrm{CH_3NH_2} > (\mathrm{CH_3})_3\mathrm{N} > \mathrm{NH_3}$. Aromatic amines are weaker bases than aliphatic amines.

Hydrocarbons

Markovnikov and anti-Markovnikov addition, Saytzeff’s rule, the acidity of terminal alkynes, and the directing effect in electrophilic substitution ($-\mathrm{OH}$, $-\mathrm{NH_2}$ and alkyl are $o,p$-directing, and $-\mathrm{NO_2}$, $-\mathrm{CHO}$ and $-\mathrm{COOH}$ are $m$-directing)

Optical isomerism

$R/S$ and $E/Z$ configurations, meso compounds, and the number of stereoisomers ($2^n$ for $n$ chiral centres, if there is no symmetry)

Haloalkanes and haloarenes

$S_N1$ goes as $3^\circ > 2^\circ > 1^\circ$ (racemisation), and $S_N2$ goes as $\mathrm{CH_3} > 1^\circ > 2^\circ > 3^\circ$ (inversion). Leaving group ability: $\mathrm{I^-} > \mathrm{Br^-} > \mathrm{Cl^-}$. Aryl halides resist nucleophilic substitution.

Alcohols, phenols and ethers

Lucas test (ZnCl$_2$ with conc. HCl): $3^\circ$ reacts at once, $2^\circ$ in about 5 minutes, and $1^\circ$ does not react at room temperature. Williamson synthesis, and the cleavage of ethers by HI.

Carbonyl compounds

Reactivity in nucleophilic addition: $\mathrm{HCHO} > \mathrm{RCHO} > \mathrm{R_2CO}$. Tests: Tollens’ and Fehling’s (aliphatic aldehydes), iodoform (for $\mathrm{CH_3CO-}$ and $\mathrm{CH_3CH(OH)-}$), and 2,4-DNP (for carbonyl compounds).

Carboxylic acids

Reactivity of the derivatives: acid chloride > anhydride > ester > amide. Hell–Volhard–Zelinsky reaction, and esterification.

Nitrogen compounds

Gabriel synthesis gives only primary amines. Hofmann bromamide degradation gives an amine with one carbon less. Carbylamine test, Hinsberg test, and the reactions of diazonium salts.

Biomolecules

Glucose (open chain and ring forms, $\alpha$ and $\beta$ anomers), reducing and non-reducing sugars, zwitterions of amino acids, levels of protein structure, and the bases in DNA and RNA. Vitamins A, D, E and K are fat-soluble.

Polymers

Addition polymers (polythene, PVC, Teflon), condensation polymers (nylon-6,6, terylene, Bakelite), natural rubber (isoprene) and Buna-S

Wurtz

$2\,\mathrm{RX}$ with Na in dry ether

$\mathrm{R-R}$

Williamson

$\mathrm{RONa} + \mathrm{R'X}$

Ether $\mathrm{ROR'}$

Reimer–Tiemann

Phenol, $\mathrm{CHCl_3}$ and NaOH

Salicylaldehyde

Kolbe

Sodium phenoxide and $\mathrm{CO_2}$

Salicylic acid

Friedel–Crafts

Benzene with $\mathrm{RCl}$ or $\mathrm{RCOCl}$ and anhydrous $\mathrm{AlCl_3}$

Alkylbenzene or acylbenzene

Gattermann–Koch

Benzene, CO and HCl with $\mathrm{AlCl_3}$ and $\mathrm{CuCl}$

Benzaldehyde

Rosenmund

$\mathrm{RCOCl}$ with $\mathrm{H_2}$ over $\mathrm{Pd/BaSO_4}$

Aldehyde

Stephen

$\mathrm{RCN}$ with $\mathrm{SnCl_2}$ and HCl, then hydrolysis

Aldehyde

Aldol

Aldehyde or ketone with $\alpha$-hydrogen, dilute NaOH

$\beta$-Hydroxy carbonyl compound

Cannizzaro

Aldehyde without $\alpha$-hydrogen, conc. NaOH

Alcohol and the salt of the acid

Haloform

Methyl ketone with $\mathrm{X_2}$ and NaOH

$\mathrm{CHX_3}$ and the carboxylate

Clemmensen and Wolff–Kishner

$\mathrm{C=O}$ with Zn–Hg and HCl (Clemmensen), or $\mathrm{NH_2NH_2}$ and KOH (Wolff–Kishner)

$\mathrm{CH_2}$

Hell–Volhard–Zelinsky

Carboxylic acid with $\mathrm{X_2}$ and red P

$\alpha$-Halo acid

Gabriel

Potassium phthalimide with $\mathrm{RX}$, then hydrolysis

Primary amine

Hofmann bromamide

$\mathrm{RCONH_2}$ with $\mathrm{Br_2}$ and NaOH

$\mathrm{RNH_2}$ (one carbon less)

Carbylamine

Primary amine, $\mathrm{CHCl_3}$ and KOH

Isocyanide

Sandmeyer

Diazonium salt with $\mathrm{CuCl}$ or $\mathrm{CuBr}$

Aryl chloride or bromide

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Atomic structure, chemical bonding and the periodic table (foundation)

2

General organic chemistry

3

Acidic and basic strength, and hydrocarbons

4

Optical isomerism

5

Haloalkanes and haloarenes

6

Alcohols, phenols and ethers

7

Carbonyl compounds

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Aldol, Cannizzaro and haloform reactions, and carboxylic acids

9

Nitrogen-containing compounds

10

Name reactions

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Oxidation and reduction reactions

12

Biomolecules

13

Polymers and chemistry in everyday life

14

Mixed previous year questions of the whole organic chemistry

15

One pass through all the mind maps, and a second look at the weak topics