Sign in
12thPass logo
New chatPYQ LibraryDoubtsRank report
Sign in to see Recents

Your guest activity stays on this device

Sign in to save progress →
Sign in

Aldehydes Ketones and Carboxylic Acids question

2017 · 9 Apr · Shift 1 · Q11
Guest · filters and generic practice availableBrowsing as a guest · PYQ filters and generic practice are available. Sign in only for personalised features and saved progress.
  1. PYQ Library
  2. /JEE Main
  3. /Chemistry
  4. /Aldehydes Ketones and Carboxylic Acids
  5. /2017 · 9 Apr · Shift 1 · Q11

Aldehydes Ketones and Carboxylic Acids question

2017 · 9 Apr · Shift 1 · Q11

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
A compound of molecular formula C8H8O2C_8H_8O_2C8​H8​O2​ reacts with acetophenone to form a single cross-aldol product in the presence of base. The same compound on reaction with conc. NaOHNaOHNaOH forms benzyl alcohol as one of the products. The structure of the compound is :
  1. A
    JEE Main 2017 (Online) 9th April Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 214 English Option 1
  2. B
    JEE Main 2017 (Online) 9th April Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 214 English Option 2
  3. C
    JEE Main 2017 (Online) 9th April Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 214 English Option 3
  4. D
    JEE Main 2017 (Online) 9th April Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 214 English Option 4
View written solutionFree

Correct answer: A

  1. Use the reaction with concentrated NaOH

    The compound gives benzyl alcohol as one of the products with conc. NaOHNaOHNaOH.

    This is characteristic of the Cannizzaro reaction, which is shown by aldehydes having no α\alphaα-hydrogen.

    Since one product is benzyl alcohol (C6H5CH2OH)\left(C_6H_5CH_2OH\right)(C6​H5​CH2​OH), the aldehyde involved must be benzaldehyde or a substituted benzaldehyde that can disproportionate to give the corresponding alcohol.

  2. Use the molecular formula

    Given formula: C8H8O2C_8H_8O_2C8​H8​O2​

    Benzaldehyde has formula C7H6OC_7H_6OC7​H6​O.

    Compared to benzaldehyde, the given compound has one extra CH2OCH_2OCH2​O unit overall, suggesting a methoxy-substituted benzaldehyde: C6H4(OCH3)(CHO)C_6H_4(OCH_3)(CHO)C6​H4​(OCH3​)(CHO) whose molecular formula is indeed C8H8O2C_8H_8O_2C8​H8​O2​

    So the compound is some methoxy benzaldehyde isomer.

  3. Use the aldol reaction clue

    The compound reacts with acetophenone to form a single cross-aldol product in base.

    In cross-aldol (Claisen–Schmidt) condensation, acetophenone provides the enolate and the aldehyde acts as the electrophile.

    For a single product, the aldehyde should not have enolizable hydrogens (true for aromatic aldehydes like methoxy benzaldehydes), and the structure should be such that no mixture of geometrical/constitutional products is expected from different reactive sites.

    Among methoxy benzaldehydes, the standard structure fitting both clues is anisaldehyde (methoxybenzaldehyde). The Cannizzaro clue is especially important: on reaction with conc. NaOHNaOHNaOH, it gives the corresponding alcohol and acid salt. If the aldehyde is ppp-methoxybenzaldehyde (anisaldehyde), it has no α\alphaα-H and undergoes Cannizzaro.

  4. Check the Cannizzaro product statement carefully

    The problem says the compound gives benzyl alcohol as one of the products. In many such questions, this points to an aromatic aldehyde without α\alphaα-H. The intended structure among the options is the benzaldehyde derivative that matches C8H8O2C_8H_8O_2C8​H8​O2​ and undergoes Cannizzaro.

    Therefore the structure is methoxybenzaldehyde, specifically the option corresponding to anisaldehyde.

  5. Match with stored answer

    The stored correct answer is A. This is consistent with the required structure.

Final Answer: A

PreviousNext

More from Aldehydes Ketones and Carboxylic Acids

  • The major product obtained in the following reaction is : Includes diagram2017 · MCQ
  • The correct sequence of reagents for the following conversion will be : Includes diagram2017 · MCQ
  • The correct statement about the synthesis of erythritol (C(CH2​OH)4​) used in the preparation of PETN is :2016 · MCQ
  • Which compound would give 5- keto -2 - methylhexanal upon ozonolysis?2015 · MCQ
  • In the following sequence of reactions: The product C is Includes diagram2015 · MCQ
  • Sodium phenoxide when heated with CO2​ under pressure at 125∘C yields a product which on acetylation products C. The major product C would be Includes diagram2014 · MCQ
  • In the reaction, the product C is: Includes diagram2014 · MCQ
  • In the given transformation, which of the following is the most appropriate reagent ? Includes diagram2012 · MCQ