MolSynapsequestion bank
MolSynapse / Question bank / Structural Identification and Practical Organic Chemistry / Structure deduction and product counting from drawn compounds
JEE Advanced levelSingle correct optionDifficulty 3 of 3si266

Compound X, , gives an orange precipitate with 2,4-DNP, no silver mirror and no iodoform precipitate. Clemmensen reduction (/HCl) of X gives the hydrocarbon shown. Which structure is X?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: C

X is a ketone (2,4-DNP positive, Tollens negative) without . Of the candidates, A and B are methyl ketones and give iodoform (A would also reduce to 2-ethyltoluene, not the hydrocarbon shown), and D is an aldehyde that gives a silver mirror. Only C, propiophenone, qualifies, and its Clemmensen product is propylbenzene (shown).
Practice Structural Identification and Practical Organic Chemistry More on Structure deduction and product counting from drawn compounds
Previous questionNext question

More questions on Structure deduction and product counting from drawn compounds