Compounds X and Y are both C,H15CI products formed in the radical chlorination of 2,4-dimethylpentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C,H14 alkene. Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C7H151 products; in this reaction Y reacts faster than X. What is the structure of X?

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
Chapter9: Nucleophilic Substitution And Β-elimination
Section9.7: Experimental Evidence For E1 And E2 Mechanisms
Problem 9.7P
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Compounds X and Y are both C,H15CI products formed in the radical chlorination of 2,4-dimethylpentane.
Base-promoted E2 elimination of X and Y gives, in each case, a single C-H14 alkene.
Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C-H151 products; in this reaction
Y reacts faster than X.
What is the structure of X?
• Do not use stereobonds in your answer.
• In cases where there is more than one possible structure for each molecule, just give one for each.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right
corner.
Separate structures with + signs from the drop-down menu.
In (F
ChemDoodle
Transcribed Image Text:Compounds X and Y are both C,H15CI products formed in the radical chlorination of 2,4-dimethylpentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C-H14 alkene. Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C-H151 products; in this reaction Y reacts faster than X. What is the structure of X? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. In (F ChemDoodle
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