Question 33 of 48
Q.(i) Write the R/S configurations of the following two chiral centres: (I) a carbon bearing OH (up), COOH (down), CH3 (right) and H (left) [i.e. lactic acid, CH3-CH(OH)-COOH, drawn in a cross projection]; and (II) a carbon bearing D (up, plain bond), NH2 (down, bold wedge) and H (right, bold wedge), with CH3 attached via a hashed/dashed bond [a deuterium-labelled 1-phenylethylamine-type stereocentre].
(ii) Write the structural formula of 'A' for the following reaction: chlorobenzene + Cl3C-CHO --(conc. H2SO4)--> A. (1 mark)
(iii) Distinguish between propanone and pentan-3-one by a suitable chemical test. (1 mark)
West Bengal WbchseWest Bengal HS (WBCHSE) Board 2019Subjective· 3mImportance★★★★★
69% · 33/48 Questions
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Start your 14-day free trial to unlock the full solution →Both stereocentres are assigned by CIP priority rules with the 'reverse if lowest priority points toward viewer' correction; the chlorobenzene + chloral reaction is the classic DDT synthesis; and the iodoform test distinguishes the two ketones because only propanone has a methyl ketone group.
- R/S configurations Centre I (lactic-acid type: OH up, COOH down, CH3 right, H left): CIP priority: . This is a Fischer-type cross where horizontal bonds (here, H) point toward the viewer. Tracing (OH→COOH→CH3) as drawn gives an apparent counterclockwise path; since the lowest-priority group (H) points toward the viewer, the apparent sense must be reversed to get the true configuration — giving clockwise = R. Centre II (D up/plain, NH2 down/wedge, H right/wedge, CH3 left/dash): CIP priority: (a C substituent outranks D, and D outranks plain H by mass). Here the lowest priority (H) is on a bold wedge (toward viewer), so again the apparent rotation of (NH2→CH3→D) must be reversed. Tracing the given positions gives an apparent clockwise path, which reverses to counterclockwise = S. (Note: the printed figure mixes wedge and plain bonds in an unusual way for a single tetrahedral centre; the above follows the CIP method as faithfully as the described geometry allows.)
- Chlorobenzene + Cl3C-CHO (chloral), conc. H2SO4: This is the industrial synthesis of the insecticide DDT: …
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