Compounds X, C9H19Br, and Y, C9H19Cl, undergo base-promoted E2 elimination to give the same single alkene product, Z. Catalytic hydrogenation of Z affords 2,3,3-trimethylhexane. In water X readily reacts to give a substitution product, C9H19OH, together with Z. Y does not react with water. Propose structures for X and Y. • . 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. 0 ? n ChemDoodle Previous

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter18: Ethers And Epoxides; Thiols And Sulfides
Section18.SE: Something Extra
Problem 36MP: Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds...
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Compounds X, C9H19Br, and Y, C9H19Cl, undergo base-promoted E2 elimination to give the same single alkene
product, Z.
Catalytic hydrogenation of Z affords 2,3,3-trimethylhexane.
In water X readily reacts to give a substitution product, C9H19OH, together with Z. Y does not react with water.
Propose structures for X and Y.
•
.
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.
0
?
n
ChemDoodle
Previous
Transcribed Image Text:Compounds X, C9H19Br, and Y, C9H19Cl, undergo base-promoted E2 elimination to give the same single alkene product, Z. Catalytic hydrogenation of Z affords 2,3,3-trimethylhexane. In water X readily reacts to give a substitution product, C9H19OH, together with Z. Y does not react with water. Propose structures for X and Y. • . 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. 0 ? n ChemDoodle Previous
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