Question

Question 27 (4 points) A compound shows an IR peak at 1740 cm! Its proton NMR spectrum consists of 2.25 ppm, quintet, 2H, 2.36 ppm, t, 4H and 3.61 ppm, 5, 6H. The most likely structure is linio Question 28 (4 points) Which one of these compounds is insoluble in water, but soluble in HCl (aq)? anisole p-methylbenzoic acid aniline ethyl amine

Answer 1

Q27)

IR peak at 1740 cm-1 is for a carbonyl group

proton NMR:

a: quintet of 2H at 2.25 ppm, for a CH2 group which has 4 neighboring H

b: triplet of 4H at 2.36 ppm, for two CH2 groups having 2 neighboring H

c: singlet of 6H at 3.61 ppm, two CH3 group bonded to electronegative atom

There are two CH2 group and two CH3 group having same chemical shift so the structure must be symmetrical.

O O Q27) a 이 - Q28) COOH - - NH2 NH2 Ethyl amine Anisole p-methylbenzoic acid Aniline

Q28)

Aniline is not soluble in water because of the hydrophobic phenyl ring but in HCl it forms salt and become soluble.

N.B- Ethyl amine is soluble in both HCl and water