Question

1. In the scheme below, treatment of 1 with the indicated reagents could yield 2 and/or 3. A second reaction would yield 4. aSpectra for question 1. 200 180 160 140 120 300. 0 Дrm 0 0 pm 200 180 160 140 120 100 30 60 40 200 200 180 160 140 120 3050 4

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Answer #1

SOLN 1

1->4 is carried out by using H2/Pd as reducing agent

a. Spectra C is of 4th molecule since it has two signal which will correspond to CH2 and CH3 group

b. Spectra D is of 1st molecule since it has 4 signal which will correspond to CH2 , CH3 , CH and terminal CH2 group

c. spectra B is of 2nd molecule since its one CH3 of two OEt group , similarly 1 signal for CH2 of OEt , one for CH and one for CH3 of main chain

d. Lastly spectra A is of 3rd molecule

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