All Exams Test series for 1 year @ ₹349 only
Question

Assign the chiral descriptors for the following molecule :

The correct answer is

S, E

The stem carries a drawn structure; the four options are text and are reproduced in full above.

Two descriptors are wanted — R/S at the stereocentre and E/Z at the double bond — and both come from the same Cahn-Ingold-Prelog priority rules.

Assigning R or S. Rank the four groups at the stereocentre by atomic number at the first point of difference, put the lowest priority group away from you, and read 1→2→3: clockwise is R, anticlockwise is S. Here bromine (Z = 35) clearly outranks every carbon substituent, so it takes priority 1.

Assigning E or Z. Rank the two groups on each carbon of the double bond separately. If the two higher-priority groups are on the same side the alkene is Z; on opposite sides, E.

The subtlety this question is really testing is isotopes. The molecule contains both C6H5 (ordinary phenyl) and C6D5 (perdeuterated phenyl). These are identical in atomic number, so the usual first test cannot separate them. CIP resolves such ties with a later rule: where atomic numbers are equal, the higher mass number takes priority. Deuterium (mass 2) therefore outranks protium (mass 1), and C6D5 ranks above C6H5.

That single decision is what makes the molecule stereochemically defined at all — without isotopic substitution the two phenyl groups would be identical and there would be no stereocentre to describe. The ester group CO2Et outranks both phenyls, because duplicated oxygen atoms at the first carbon beat the carbons of an aromatic ring.

Per the official final answer key the answer is option (A), S and E.

Was this answer helpful?

Similar Questions

  1. Complete the following reaction by suggesting the appropriate substrates (I & II) :

  2. Suggest most suitable conditions for the following selective conversion :

  3. What major product is isolated from the following reaction :

  4. Predict stereochemical outcome of the following reaction :

  5. The major product of the following reaction is :

  6. Predict the major product of the following reaction :

  7. The major product of the following reaction is :

  8. The major product of the following reaction is :

  9. The major product formed in the following reaction is :

  10. The major product formed in the following reaction is :


Important Questions from Chemistry in Everyday Life

  1. Which of the following is a greenhouse gas?

    I. Methane

    II. Nitrous oxide

  2. The gas which turns lime water milky is:

  3. Liquefied Petroleum Gas (LPG) is mainly a mixture of:

  4. Among the following, the conducting form of carbon is

  5. Which of the following is NOT a Fossil Fuel?

Need Expert Advice?
Test Series
MAHA Teacher img
Teaching
MAHA TAIT Mock Test Series (New)
58 Tests 1 Tests Free
3821 Attempts
4.9(108)
English, Hindi, Marathi

Start Your Preparation with Prepp Mobile App

Download the app from Google Play & App Store
Download the app from Google Play & App Store
Prepp Mobile App