Compound A (CH18O) forms a phenylhydrazone, but it gives a negative Tollens' test. The IRspectrum of A has a strong band near 1710 cm-1. The broadband carbon NMR spectrum of A isgiven below.a) Propose a structure for A and explain how your structure fits the spectral data.b) Propose a mechanism for the formation of phenylhydrazoneCH,A, CyH0CH,CHCDC,TMS220200180160140120100806040208 (ppm) The manager of an organic chemistry stockroom prepared unknowns for a 'Ketone andAldehyde experiment by placing two drops of the liquid unknowns in test tubes labelled A andB. He then stored the test tubes for several days until they were needed. On the day of theexperiment, the students complained the IR spectrum measured for test tube A is different fromthe spectrum shown by the stockroom manager at the end of the class (refer the picture below).Obviously something has happen to the solution while being left for a few days.Test tube A - managerTest tube A - students271028103000 cm 1725 cm3000 cm-11710 cmstockroom managers' spectrumstudents' spectruma) Identify the functional group revealed by the IR spectrum ofį. The stockroom managerii. The studentsb) Explain the reason of discrepancy between the stockroom manager's spectrum and thestudent's results.c) Suggest how this misunderstanding might be prevented.

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spectrum of A has a strong band near 171io cm-1. The broadband carbon NMR spectrum given below. a) Propoke a structure for A and explain how your structure fits the spectral data. b) Propose a mechanism for the formation of phenylhydrazone CH.

spectrum of A has a strong band near 171io cm-1. The broadband carbon NMR spectrum given below. a) Propoke a structure for A and explain how your structure fits the spectral data. b) Propose a mechanism for the formation of phenylhydrazone CH.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Question

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Compound A (CH18O) forms a phenylhydrazone, but it gives a negative Tollens' test. The IR
spectrum of A has a strong band near 1710 cm-1. The broadband carbon NMR spectrum of A is
given below.
a) Propose a structure for A and explain how your structure fits the spectral data.
b) Propose a mechanism for the formation of phenylhydrazone
CH,
A, CyH0
CH,
CH
CDC,
TMS
220
200
180
160
140
120
100
80
60
40
20
8 (ppm)

The manager of an organic chemistry stockroom prepared unknowns for a 'Ketone and
Aldehyde experiment by placing two drops of the liquid unknowns in test tubes labelled A and
B. He then stored the test tubes for several days until they were needed. On the day of the
experiment, the students complained the IR spectrum measured for test tube A is different from
the spectrum shown by the stockroom manager at the end of the class (refer the picture below).
Obviously something has happen to the solution while being left for a few days.
Test tube A - manager
Test tube A - students
2710
2810
3000 cm 1725 cm
3000 cm-1
1710 cm
stockroom managers' spectrum
students' spectrum
a) Identify the functional group revealed by the IR spectrum of
į. The stockroom manager
ii. The students
b) Explain the reason of discrepancy between the stockroom manager's spectrum and the
student's results.
c) Suggest how this misunderstanding might be prevented.

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