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Choose the Best Answer · Q20

Q.Propyne on passing through red hot iron tube gives

(a) 1,3,5-trimethylbenzene (a benzene ring carrying -CH3 groups at the 1, 3 and 5 positions)
[Note: only option
(a) is printed against this question in the source textbook -- no options (b), (c),
(d) are present on the page; this gap is preserved honestly rather than invented.]
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Step 1. Passing ethyne (acetylene) through a red-hot iron tube trimerises three molecules into benzene (met earlier, under both alkyne polymerisation and benzene-preparation-from-acetylene) -- a cyclic trimerisation of the triple bond.

Step 2. Propyne, CH3-C≡\equivCH, undergoes the exact same cyclic trimerisation under the same conditions; each of the three propyne units contributes its two triple-bond carbons to the new benzene ring, while each retains its own methyl substituent. …

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