[smdelgado]

Hi all!
Can someone help me identify reaction conditions (reagents and conditions) from A:


to B:


Thanks in advance!

[sharbeldam]

You need to show your try, are you in college? have you learned alkene reactions? markovnikov's rule?

[smdelgado]

OK think I got it with some help from your hint. The reaction can be performed in aqueous solution with sulfuric acid catalyst. Does that sound right?

And no, I'm not a college student. This is a small piece of a pretty large and difficult problem set of interview questions. The questions are open book, open-world (we can reach out to anyone) and range in topics from math, engineering, biology, chemistry, you name it. Thanks for the *delete me*

[AWK]

Bad association. This isomer can be obtained according to the anti-Markovnikov mechanism. This is quite advanced organic chemistry.

[mjc123]

Mark/anti-Mark? This isn't an addition - count the carbons!

[hollytara]

Good catch by MJC - the chain is shorter in the product....

[sharbeldam]

Indeed good catch! maybe ozonlysis and reduction...

[smdelgado]

Thanks all!