(3) From the spectral data (1H, 13C NMR, IR, MS) you were given, identify the st
ID: 527511 • Letter: #
Question
(3) From the spectral data (1H, 13C NMR, IR, MS) you were given, identify the structure of your product. Explain why you chose your particular product based on the spectroscopic data. You will not receive full marks for determination of the unknown unless you explain why.
(4) Fully assign the 1H NMR spectrum of your product (i.e. determine which peaks in the 1H NMR correspond to which hydrogens in the product). You will not receive full marks for determination of the unknown unless you assign the 1H NMR spectrum completely.
When performing your assignment, p34 of the lab handout will be indispensable...
ck control BRUKER 1500 2000 2500 3000 3500 Wave number cm-1 C IOPUS 72.139. 1294IMEASIEXP 4 T.57 EXP 4 PRODUCT nstrument type and/or accessory PRODUCT Page 1/1 1000 500 5/2/2017Explanation / Answer
Starting aldehyde
1.1 ppm (singlet, 9H) for tert-butyl group
9.5 ppm (singlet, 1H) for aldehydic CH
Structure,
(CH3)3C-CHO
Starting amine
2.2 ppm (singlet, 3H) for CH3 next to Ph ring
two doublets in the downfield region is for the phenyl protons
3.4 ppm (broad singlet) for NH2 protons
Structure,
CH3-C6H4-NH2
Reductive amination forms as amine,
(CH3)3C-CHO + CH3-C6H4-NH2 --> (CH3)3C-CH2-NH-C6H4-CH3 (product)
M+ 177
It shows 3 peaks in the upfield region of 1H NMR for CH3, CH2 and (CH3)3 protons and two doublets in the downfield region for aromatic protons. A broad singlet is for NH proton
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