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JEE Advanced 2019 Paper 2 · Chemistry · General Organic Chemistry and Isomerism · hard

JEE Advanced 2019 Paper 2 Chemistry: Paragraph 2

List-I lists four compounds, each written without any stereochemical descriptor, and List-II lists six numbers. Count stereoisomers as distinct compounds, each enantiomer counted separately, and include geometrical isomers.

List-I: (P) CH3CH=CH−CH=CH−CH3\mathrm{CH_3CH=CH-CH=CH-CH_3} (Q) CH3CH(OH)CH(OH)CH(OH)CH3\mathrm{CH_3CH(OH)CH(OH)CH(OH)CH_3} (R) CH3CH=CH−CH(Br)−CH(Cl)CH3\mathrm{CH_3CH=CH-CH(Br)-CH(Cl)CH_3} (S) CH3CH(Br)−CH=CH−CH(Br)CH3\mathrm{CH_3CH(Br)-CH=CH-CH(Br)CH_3}

List-II: (1) 00 (2) 22 (3) 33 (4) 44 (5) 66 (6) 88

Question 1

Single correct option

Match each compound in List-I with its total number of stereoisomers, given in List-II.
  1. A. P→3, Q→4, R→6, S→6
  2. B. P→3, Q→6, R→6, S→5
  3. C. P→4, Q→4, R→6, S→5
  4. D. P→3, Q→4, R→6, S→5
Show answer and solution

Answer: (D) P→3, Q→4, R→6, S→5

(P) Hexa-2,4-diene has two stereogenic double bonds with identical ends, so the E,Z and Z,E forms are the same compound: EE, ZZ, EZ =3=3, so P→3. (Q) Pentane-2,3,4-triol has stereocentres C2 and C4 (identical environments) and C3, a pseudoasymmetric centre. This gives 44 stereoisomers: two meso forms (r and s at C3) and one enantiomeric pair, so Q→4. (R) There is one double bond (2 forms) and two unlike stereocentres (4 forms): 2×4=82\times4=8, so R→6. (S) The double bond (E or Z) and two identical stereocentres: for each geometry RR, SS and meso, so 2×3=62\times3=6, giving S→5. The correct code is P→3, Q→4, R→6, S→5; the others reflect treating P as 2×22\times2, treating S as unsymmetrical (88), or Q as unsymmetrical (88).

Question 2

Single correct option

Match each compound in List-I with the number of its stereoisomers that are optically active, given in List-II.
  1. A. P→1, Q→2, R→6, S→4
  2. B. P→1, Q→4, R→6, S→4
  3. C. P→3, Q→2, R→6, S→4
  4. D. P→1, Q→2, R→6, S→5
Show answer and solution

Answer: (A) P→1, Q→2, R→6, S→4

Optically active stereoisomers are the total number minus the achiral ones. (P) All three isomers (EE, ZZ, EZ) of hexa-2,4-diene have a mirror plane in the molecular plane, so 00 are active, P→1. (Q) Of the 44 stereoisomers of pentane-2,3,4-triol, two are meso (achiral) and two are enantiomers, so 22 are active, Q→2. (R) With no element of symmetry, all 88 stereoisomers are chiral, so R→6. (S) Of the 66 stereoisomers, the E-meso and Z-meso forms are achiral; the other 44 (RR and SS for each geometry) are optically active, so S→4. The correct code is P→1, Q→2, R→6, S→4. Distractors count all four triol isomers as active, count all three hexadiene isomers as active, or count the meso forms of S as active.
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