Bromobenzene -----> triphenyl carbinol via Grignard reaction (a) How could you follow this reaction using spectroscopy,...

Bromobenzene -----> triphenyl carbinol via Grignard reaction

(a) How could you follow this reaction using spectroscopy, IR, NMR? Be specific.

(b) How could you follow this reaction using TLC? Be specific. (6 pts.)

Expert Solution

IR: Bromobenzene shows aromatic C-H(3050) and C=C(1640) peaks and C-Br (650) peak in fingerprint region while triphenylcarbinol shows aromatic C-H and C=C peaks and intense broad peak at 3500-3300 due to O-H bond

NMR: Bromobenzene shows a multiplet in the aromatic region 6.5-7.5 (5H) while triphenyl carbinol shows a little peak in the range 3.5-4.5 due to O-H proton in addition to aromatic protons(15H)

b) Bromobenzene is nonpolar while triphenyl carbinol is slightly polar due to presence of O-H group thus triphenyl carbinol moves slowly with a nonpolar eluting solvent (hexane) thus will have small Rf value than bromobenzene

queen_honey_blossom answered 2 years ago

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