University of Yaounde 1.

Faculty of Science
Department of Organic Chemistry
Continuous Assessment Test. 1st Semester 2022/2023. 2Hrs

Read carefully the following text and give a concise and clear answer to each of the questions
that follows.

An unknown organic compound which has the molecular mass 230 contains 78.26% carbon and
7.83% hydrogen has no reaction with FeCl3 solution but decolorizes a solution of bromine in
CCl4. It also gives a white precipitate with Ammoniacal AgNO3 solution and yellow crystals with
2,4-dinitrophenyl hydrazine.

Its infrared spectrum displayed strong absorption bands at 3300, 3050, 2920, 2850, 2120, 1715,
1600 and 1500 cm-1 while its 1H NMR had signals for protons at δ (ppm): 6.84 (2H, d, 8.1Hz);
6.21 (2H, d, 8.1Hz); 3.86 (3H, s); 2.22 (1H, q, 6.5Hz); 1.98 (1H, s); 1.34 (6H, s); 1.31 (3H, d, 6.5Hz).
Ion fragments found in its EIMS included those with mass at m/z (%): 230(4); 177(8); 149(100);
81(18) and 53(46).

Questions:

1) What is the molecular Formula of this compound?

2) Use the given information to find the structure of the unknown compound. Show clearly

how you arrived at your structure.

3) Assign all proton resonances

4) Show that the functional groups in your structure can give the absorption bands listed in

the IR data.

5) Give the structures of the ions fragments the masses of which are given in the text.

Given: C : 12 H:1 O : 16 N : 14

CONTACT COORDONNATEUR 6 76 35 34 07
 FACULTY OF SCIENCE DEPARTMENT OF ORGANIC CHEMISTRY
CONTINUOUS ASSESSMENT TEST CHM 311 1st SEMESTER 2018-2019

Study the following analytical data for an organic compound, W, obtained from the seeds of the
orange fruit and answer all the questions that follow.

W. White micro crystals, Mp 98°C (acetone). HRESIMS: m/z 175.0968 [M+H]+. Elementary analysis:
C 55.17%; H 8.05%. Analytic test: Gives yellow crystals with 2,4-dinitro phenyl hydrazine. IR (KBr
disc) ν cm-1: 2918, 2852, 1740, 1714, 1452, 1387, 1235 and 1208. EIMS (70Ev, 200°C), m/z (%):
175(1); 174(6); 143(21); 131(8); 115(38); 101(100); 59(11) and 43(38). 1H NMR See table 1

Table 1: W (400 MHz 1H, DMSO d6)

address Frequency (Hz) intensity

1 1680 246
2 1440 369
3 840 369
4 560 738

Questions:

1) What is the molecular Formula of W?

2) How many unsaturated sites has W?

3) Calculate the corresponding chemical shifts and integration of the proton families given in

Table 1.

4) Use all the analytical data given to find the right structure of W.

5) Assign all proton resonances

6) Give the structures of the ions fragments the masses of which are given in the text.

CONTACT COORDONNATEUR 6 76 35 34 07