Organic Chemistry / Carbocation Intermediate Rearrangements
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Solution: Select the compound in each of the following pairs that will...

Question

Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice.

 (e) 1-Methylcyclopentanol or cyclohexanol 

Video Transcript

Hey everyone, so let's take a look at these two compounds and figure out which one of them is going to be more reactive towards hydrogen bromide to get the corresponding alkyl bromide. So, just imagine that both of these compounds are being subjected to HBr, which one you think that I react the fastest? Well, all we need to do is compare our alcohols. So, how are you going to compare them? they're both on a ring, right? But I tried to help you out by drawing in this hydrogen here, now the reason I did that is because one of these alcohols is a tertiary and we know the tertiary alcohol is going to react faster than a secondary and a secondary reacts faster than a primary alcohol. So, which one of these compounds contains the tertiary alcohol? Well, it's going to be the one on the left, because here this carbon is connected to three other carbons. So, for that reason we're going to our a tertiary alcohol is going to react faster than just our secondary, okay? So the compound that wins is the one on the left. alright guys, so hopefully this makes sense and let me know if you have any questions