Haloalkane with molecular formula, C,H,CI has four structural isomers, A, B, C and D. The structure of A, B and C are shown below. A - (CH3)3CCI B - CH3(CH2)3CI C - CH3CH(CI)CH₂CH3 Give the IUPAC names and classification for isomers A, B and C, respectively.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter2: Alkanes And Cycloalkanes
Section: Chapter Questions
Problem 2.61P: Following are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used...
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Haloalkane with molecular formula, C,H,CI has four structural isomers, A, B, C and D. The structure of A, B and C are shown below.

A - (CH3)3CCI

B - CH3(CH2)3CI

C - CH3CH(CI)CH₂CH3

Give the IUPAC names and classification for isomers A, B and C, respectively.

Arrange isomers A, B and C in ascending order of their reactivity with respect to SN1 reaction. Explain your answer.

Write the reaction equations involved for the reaction of the most reactive isomer among A, B and C, with respect to SN1 reaction with aqueous KCN, in ethanol under reflux. Show the reaction mechanism.

Draw the structure and give IUPAC name of isomer, D.

Isomer D reacts with magnesium in anhydrous ether producing an alkyl magnesium chloride E which is then hydrolyzed and produced F, C4H10. Elimination of D with ethanolic KOH under reflux produces G. The treatment of D with sodium metal in ether solvent yields a symmetry alkane H, C8H₁8, which possesses two tertiary carbons. Hydrolysis of D with aqueous sodium hydroxide solution under reflux produces alcohol I.

Draw reasonable structures of E, F, G, H, and I.

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