7. (8 pts) Sometimes, things happen that make you scratch your head and go "huh - that's weird", even though it goes against the "rules". This is one of those reactions. Someone was reacting the following reagents expecting to create a hydrate (You don't know much about these: but it's the thing in the "not this" box). That's not the final product. Instead, they found that the product looked a little different when they went to take an NMR spectrum and IR spectrum. Draw me a chemical mechanism for how this compound reacted and lost a carbon, the mechanism, and why it is oddly reasonable to break a C-C bond in this one uncommon case.
IR:
OH
Excess NaOH
CI
CI
CI
then HCI
recrystallized
OHCI
CI
NOT THIS
Actual product
(your prediction)
40
30
1570
20
10
3400
2935
1770
1413
0
4000
1718
3000
2000
1500
v (cm?¹)