Mistakes in Road Map

[marymatthews]

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Are there any mistakes in the DAT Destroyer Organic Chem Road Maps? Are all the Road Map reactions flawless?
Thanks

 

[marymatthews]

For example, Road Map 2, the reaction with K2Cr2O7, with ethylbenzene, you lose a carbon to form COOH?
Or, Road Map 2, it says Br2, hv or NBS, ROOR, heat. I thought Br2, hv was selective and Br went for tertiary carbon. But, NBS, ROOR, heat goes for primary?

 

[rejuvenatedsoul]

^i think K2Cr2O7 oxidizes alkyl chains on benzenes down to COOH no matter what the chain length...saw this in an achiever question as well as destroyer.

 

[theragu]

For example, Road Map 2, the reaction with K2Cr2O7, with ethylbenzene, you lose a carbon to form COOH?
Or, Road Map 2, it says Br2, hv or NBS, ROOR, heat. I thought Br2, hv was selective and Br went for tertiary carbon. But, NBS, ROOR, heat goes for primary?

K2Cr2O7 will oxidize for COOH no matter the alkyl chain, as the previous poster said.

I also noticed the differences with Br2, hv..there are a few reactions on the road maps with it.
From what I've gathered, it seems that with a double bond or a benzylic carbon, Br2-> hv will add primary; otherwise it will add zaitsev, as normal.

 

[RING12]

if you use Br2/oh you lose one carbon. jones reagent on bezen ring become cooH no matter what -R you have on it. and NBS OR radical takes hydrogen from allylic or benzylic hydrogen bc of hyperconjugation and resonance and this is different from being Br is better than Cl. all road maps are correct. my ochem teacher was a very great and hard teacher like orgoman. or even I can say he was harder. and he covered all the stuff are in this book.