Question

Can you help me identify reagent (i), Compound 8 and Compound 12 in the reaction scheme?

Scheme 5: Compound 8 Compound 11 H CH2 CH3 (1) Compound 12 NaBH4 CH3OH OH OH NO2

You have laboratory data on all the compounds in the synthesis, however the amount of data available to you varies. Some have the entirety of the spectral data, others have as little as the elemental analysis. Use the laboratory data to help you discover which reaction has been performed.

The lab data for Compound 8 and 12 is as follows:

Compound 8: MW: 314.38 C: 72.59 H: 7.05 H NMR: Indicates a 1,2,4-trisubstituted aromatic ring 13C NMR: 200 180 160 140 120 8

Compound 12: MW: 531.61 C: 70.04 H: 6.26 N: 2.63

You can use any of the following reaction types, but you will not need to use any reaction more than once:

1. Syl a. Reagents: HCl or HBr and an alcohol. b. Uses: Convert tertiary alcohols to more synthetically useful tertiary alkyl

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