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At what position would you expect to observe IR absorptions for the following molecules?

a.

b.

c.

d.

Short Answer

Expert verified
  1. A 5-membered ring ketone has IR absorption at1750 c³¾-1 , and anα,β -unsaturated ketone has IR absorption at1685 c³¾-1 .
  2. A 5-membered ring and aromatic ketone both have IR absorption at 1720 c³¾-1.
  3. A 5-membered ring ketone has IR absorption at 1750 c³¾-1.
  4. Aromatic aldehyde has IR absorption at 1705 c³¾-1,2720 c³¾-1 and2820 c³¾-1 . Aliphatic ketone has IR absorption at 1715 c³¾-1.

Step by step solution

01

IR absorptions

For simple aldehydes and ketones, a strong IR absorption is seen between the range 1710-1740 cm-1, but due to the presence of conjugation of C=O by phenyl ring or double bond, the stretching frequency gets lowered.

02

The IR absorptions in 4-Androstene-3,17-dione

(a) In 4-Androstene-3,17-dione, only carbonyl absorptions are noted. A 5-membered ring ketone has IR absorption at 1750 c³¾-1and an α,β-unsaturated ketone has IR absorption at 1685 c³¾-1.

IR absorption in (a)

03

The IR absorptions in 1-Indanone

(b) In 1-Indanone, there is a 5-membered ring and aromatic ketone. Both these have IR absorptions at 1720 c³¾-1.

IR absorption in (b)

04

The IR absorptions in compound (c)

(c) In the given compound, there is a 5-membered ring ketone. It has IR absorption at 1750 c³¾-1.

IR absorption in (c)

05

The IR absorptions in compound (d)

(d) There is one aromatic aldehyde and one aliphatic ketone in the given compound. Aromatic aldehyde has IR absorption at 1705 c³¾-1, 2720 c³¾-1, and 2820 c³¾-1. Aliphatic ketone has IR absorption at 1715 c³¾-1.

IR absorption in (d)

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