JEE Chemistry Organic Chemistry Mixed Topics Notes Set 01

Revision Notes for JEE Chemistry: Organic Chemistry Mixed Topics

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Review Organic Chemistry Mixed Topics for JEE Chemistry

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Nomenclature

1. Choose the principal functional group by priority (acid, ester, amide, nitrile, aldehyde, ketone, alcohol, amine). It takes the lowest locant and appears as the suffix; other groups are prefixes.
2. SH as a substituent is called mercapto or sulfanyl. For \(\ce{HOCH2CH(SH)CH2SH}\) the name is 2,3-dimercaptopropan-1-ol.
3. \(\ce{(CH3)2CHCN}\) is 2-methylpropanenitrile, also called isopropyl cyanide or isobutyronitrile.
4. Carboxylic acid series: formic, acetic, propionic, butyric, valeric. The amide of crotonic acid is crotonamide.

Isomerism and Hybridisation

1. A chiral carbon has four different groups. A plane of symmetry rules out optical activity.
2. Fischer projections: a meso compound and a chiral stereoisomer of the same constitution are diastereomers.
3. E/Z: assign CIP priorities on each alkene carbon. Higher priorities on the same side give Z, on opposite sides give E.
4. A double bond in a six-membered ring cannot be trans, but two substituents on different ring carbons can be cis or trans.
5. Carbons with three sigma bonds are \(sp^2\), with two are sp. Count a triple bond as 1 sigma and 2 pi bonds.
6. Secondary amines of formula \(\ce{C4H11N}\): three structural isomers.

Reactions

ReactionPoint to remember
Aldol condensation of cyclohexanonealdol addition, then loss of water on heating gives the conjugated enone
Hydrogenation over Pd/C at 1 atmreduces C=C in preference to C=O
Intramolecular Cannizzaro of phthalaldehydehydroxy acid, which closes to the lactone phthalide on heating with acid
Gabriel phthalimide synthesisgives primary aliphatic amines only
Carbylamine testprimary amine with chloroform and KOH gives an isocyanide with a foul smell
Sucrosenon-reducing sugar, because no free anomeric group is left

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