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Q.(i) Write the IUPAC names of the following: (A) CH2=CH-CH(CH3)-CH2-CH2-C(triple bond)CH (B) CH3-CH(Cl)-CH2-CH2-C(=CH2)-CH3

(ii) Write short notes on: (A) Hyperconjugation (B) Carbon free radical
(iii) In which compounds does a nucleophilic addition reaction occur? Explain.
Rajasthan RbseRajasthan Board Senior Secondary Part-I Examination 2018Subjective· 5mImportance★★★★★
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The two structures are named 3-methylhept-1-en-6-yne and 5-chloro-2-methylhex-1-ene; hyperconjugation and free radicals are both stabilised by adjacent C–H sigma bonds; and nucleophilic addition is characteristic of polar-multiple-bond compounds like carbonyls.

(i) IUPAC names:

(A) CH2=CH-CH(CH3)-CH2-CH2-C(triple bond)CH: The longest chain containing both multiple bonds has 7 carbons, with a double bond and a triple bond, so it is named as a 'hept-en-yne'. Numbering from the double-bond end gives the double bond the lower locant (1) and the triple bond locant 6 (the same overall locant set {1,6} results numbering from either end, and by convention the double bond is given the lower number when there is a choice). This places the methyl branch at C3.

Name: 3-methylhept-1-en-6-yne.

(B) CH3-CH(Cl)-CH2-CH2-C(=CH2)-CH3: since a double bond must be included in the principal chain wherever possible, the longest chain is chosen through the exocyclic =CH2 carbon, giving a 6-carbon chain with the double bond, a chlorine substituent, and a methyl branch. Numbering from the end nearer the double bond gives it locant 1 (lower than numbering from the other end, which would give locant 5) — this takes priority over giving the substituents the lowest locants.

Name: 5-chloro-2-methylhex-1-ene.

(ii)(A) Hyperconjugation: This is a permanent electronic effect in which electron density from a C–H (or C–C) sigma bond of an alkyl group attached to an unsaturated centre (double/triple bond, carbocation or free radical) delocalises into the adjacent empty or π orbital, through partial overlap of the sigma bond with that orbital. Because no formal bond is broken, it is sometimes called 'no-bond resonance'. It explains why more highly substituted alkenes, carbocations, and free radicals are more stable — more C–H bonds on the adjacent (alpha) carbon means more hyperconjugative structures and greater stabilisation.

(ii)(B) Carbon free radical: A carbon free radical is an electrically neutral carbon species carrying one unpaired electron, formed by homolytic bond cleavage. It is highly reactive and short-lived, and is generally considered to have a near sp2 hybridised, planar (or shallow pyramidal) geometry with the unpaired electron in a p-orbital. Like carbocations, free-radical stability follows the order 3° > 2° > 1° > methyl, due to the +I effect and hyperconjugative stabilisation from attached alkyl groups.

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