GATE CY Experimental techniques in organic chemistry PYQs & Answers

Questions 1–5 of 5. Imported answers require independent review unless marked reviewed.

Compound K displayed a strong band at 1680 cm

in its IR spectrum. Its

H-NMR spectral data are as follows:

(ppm) 7.30 (d, J = 7.2 Hz, 2H), 6.8 (d, J = 7.2 Hz, 2H), 3.8 (septet, J = 7.0 Hz, 1H), 2.2 (s, 3H), 1.9 (d, J = 7.0 Hz, 6H). The correct structure of compound K is

Your answerChoose one option.

Structure shown in figure

Structure shown in figure

Diagram for Chemistry question 42 (figure 2)

Structure shown in figure

Diagram for Chemistry question 42 (figure 3)

Structure shown in figure

Diagram for Chemistry question 42 (figure 4)

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A compound,

, has the following spectral data;

NMR (ppm): 9.16 (s), 6.89 (d,

Hz), 6.64 (d,

Hz), 1.53 (s)

NMR (ppm): 154.7, 140.9, 127.1, 114.4, 40.7, 30.7

The structure of the compound is

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Diagram for Chemistry question 36 (figure 2)

Diagram for Chemistry question 36 (figure 3)

Diagram for Chemistry question 36 (figure 4)

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A compound with molecular formula C

showed a strong IR band at ~ 1720 cm

, a peak at m/z 122 in the mass spectrum and the following

H NMR signals: δ 8.1–8.0 (2H, m), 7.6–7.5 (1H, m), 7.5–7.3 (2H, m), 4.3 (2H, t), 1.8 (2H, sextet) and 1.0 (3H, t). The structure of the compound is:

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Diagram for Chemistry question 29 (figure 2)

Diagram for Chemistry question 29 (figure 3)

Diagram for Chemistry question 29 (figure 4)

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In the electron ionization (EI) mass spectra, methyl hexanoate, methyl heptanoate and methyl octanoate give the same base peak. The m/z value of the base peak is _____.

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The spectroscopic data for an organic compound with molecular formula C₁₀H₁₂O₂ are given below. IR band around 1750 cm⁻¹, ¹H NMR δ 7.3 (m, 5H), 5.85 (q, 1H, J = 7.2 Hz), 2.05 (s, 3H), 1.5 (d, 3H, J = 7.2 Hz) ppm. The compound is

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methyl 2-phenylpropionate

1-(phenylethyl) acetate

2-(phenylethyl) acetate

methyl 3-phenylpropionate

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GATE CY Experimental techniques in organic chemistry PYQs

How to practice Experimental techniques in organic chemistry

Question 42

Question 36

Question 29

Question 25

Question 50