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OMLx2 1 Online A cempound, C,,0.exhibits IR absorption at 1705 em, Its carbon NM

ID: 953192 • Letter: O

Question

OMLx2 1 Online A cempound, C,,0.exhibits IR absorption at 1705 em, Its carbon NMR shifts are given below. The number of hydrogess at cach carbon, determined by DEPT, is given in parentheses afher the chemical shift CNMR: 8140)1344(21460 (, 1947) Draw the stracture of this compound in the wirdow below . You do net have to consider stereochomistry You do net have to consider sterechonistry You do net have to esplicily draw H atomms De sot inchade losc pairs in your anwwo. They will sox be considered in the grading · lneases where there is more than one answer, Just draw one. WE rehurn commandoption

Explanation / Answer

The molecular formula C4H6O indicates two degreesof unsaturation.

From the IR value of 1705, one unsaturation can be taken as a carbonyl group and other can be a double bond.

From the 13C data, the peak at 14with 3 hydrogens is for a methyl group and the peak at134 for a double bonded CH2 and the peak at 146 is for double bonded c with no H and one at 194 is for carbonyl -CHO(one H) .

Thus the structure is CH2 =C(CH3)CHO