3 Russian Chemists Set Out To Dehydrate 1 Cyclobuty Lethanol By Treating It With A Strong Acid And Heat As Shown Below 1 (76.02 KiB) Viewed 33 times
3 Russian Chemists Set Out To Dehydrate 1 Cyclobuty Lethanol By Treating It With A Strong Acid And Heat As Shown Below 2 (11.07 KiB) Viewed 33 times
3. Russian Chemists set out to dehydrate 1- cyclobuty lethanol by treating it with a strong acid and heat as shown below. However, they found the product to be a 5 membered ring compound, 1-methylcyclo pentene. Using curved arrows, write a detailed (mechanism for this overall reaction, showing the 4 positively charged intermediates A-D A (labels below) en route from the starting material to the l-methylcyclopentene product. For the acid you may just use "H-h”. To help " you, here are the key words in sequence describing the mechanistic steps: 1) Protonation of starting alcohol to form A (2) Water loss to form B (3) Cation rearrangement to form C (4) Hydrick migration to form D 5) Proton loss to form 1-methylcyclopentene Don't forget to work both backward and forward; Where do you protonate the starting alcohol to form A? But also what is the species D that Jose H* to yield l-methylcyclo pertene. ca (Picture of reaction is included below!)
OH Acid H-A Heat 1-cyclobutylethanol 1-methylcyclopentene A B с D
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