If we were to determine the acidity of substituted carbons, you would find the following order:
RC≡CH>R2C=CH2>RCH3
From this, we should think an sp carbon is more electron withdrawing than an sp2 carbon which in turn is more electron withdrawing than an sp3 carbon. In a Friedel Crafts alkylation reaction, we require the intermediate to be a carbocation. From the information we just considered, rate the stability of the following carbocations?
RC≡C+, R2C=CH+, and RCH2+
The problem is not with the Lewis acid used, but the difficulty in forming the required sp2-carbocation intermediate.