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Using acetylene and 2-methylpropane as your only sources

Chapter 11, Problem 11.44

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QUESTION:

Using acetylene and 2-methylpropane as your only sources of carbon atoms, propose a plausible synthesis for CH3COCH2CH(CH3)2. You will need to utilize many reactions from previous chapters.

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QUESTION:

Using acetylene and 2-methylpropane as your only sources of carbon atoms, propose a plausible synthesis for CH3COCH2CH(CH3)2. You will need to utilize many reactions from previous chapters.

ANSWER:

Step 1 of 10

(a)

Cyclopentane is a symmetrical molecule, and all the ten hydrogens on the five carbons are equivalent.

So, monochlorination of cyclopentane produces only one constitutional isomer.

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