The relative reactivity of hydrogens in 90 % CH 3 CH 2 CHBr 2 , 8.5 % CH 3 CHBrCH 2 Br and 1 .5 % BrCH 2 CH 2 CH 2 Br formed should be calculated and compared with similar results of bromination with propane. Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism. Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation. The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Question

Five isomeric alkenes. A through each undergo catalytic hydrogenation to give 2-methylpentane The IR spectra of these five alkenes have the key absorptions (in cm Compound Compound A –912. (§), 994 (5), 1643 (%), 3077 (1) Compound B 833 (3), 1667 (W), 3050 (weak shoulder on C-Habsorption) Compound C Compound D) –714 (5), 1665 (w), 3010 (m) 885 (3), 1650 (m), 3086 (m) 967 (5), no aharption 1600 to 1700, 3040 (m) Compound K Match each compound to the data presented. Compound A Compound B Compound C Compound D Compound

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Chapter 3, Problem 40P

Interpretation Introduction

Interpretation: The relative reactivity of hydrogens in 90 % CH3CH2CHBr2 , 8.5 % CH3CHBrCH2Br and 1.5 % BrCH2CH2CH2Br formed should be calculated and compared with similar results of bromination with propane.

Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary C – H bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

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Five isomeric alkenes. A through each undergo catalytic hydrogenation to give 2-methylpentane The IR spectra of these five alkenes have the key absorptions (in cm Compound Compound A –912. (§), 994 (5), 1643 (%), 3077 (1) Compound B 833 (3), 1667 (W), 3050 (weak shoulder on C-Habsorption) Compound C Compound D) –714 (5), 1665 (w), 3010 (m) 885 (3), 1650 (m), 3086 (m) 967 (5), no aharption 1600 to 1700, 3040 (m) Compound K Match each compound to the data presented. Compound A Compound B Compound C Compound D Compound

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