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Aldehydes Ketones and Carboxylic Acids question

2020 · 8 Jan · Shift 2 · Q3
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Aldehydes Ketones and Carboxylic Acids question

2020 · 8 Jan · Shift 2 · Q3

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
An unsaturated hydrocarbon X absorbs two hydrogen molecules on catalytic hydrogenation and also gives following reaction : JEE Main 2020 (Online) 8th January Evening Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 180 English B(3 - oxo - hexanedicarboxylic acid) X will be :-
  1. A
    JEE Main 2020 (Online) 8th January Evening Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 180 English Option 1
  2. B
    JEE Main 2020 (Online) 8th January Evening Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 180 English Option 2
  3. C
    JEE Main 2020 (Online) 8th January Evening Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 180 English Option 3
  4. D
    JEE Main 2020 (Online) 8th January Evening Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 180 English Option 4
View written solutionFree

Correct answer: C

  1. Interpret the information given

We are told that hydrocarbon XXX:

  • is unsaturated,
  • absorbs two molecules of hydrogen on catalytic hydrogenation.

This means XXX has a total of two units of pi-bond unsaturation that can be hydrogenated. So XXX could contain:

  • two double bonds, or
  • one triple bond, etc.

Also, on reaction, it gives B=B =B= 3-oxo-hexanedicarboxylic acid.

Let us write the structure of 3-oxo-hexanedicarboxylic acid.

Hexanedicarboxylic acid means a 6-carbon chain including two terminal carboxyl groups:

HOOC-CH2−CO-CH2−CH2−COOH\text{HOOC-CH}_2-\text{CO-CH}_2-\text{CH}_2-\text{COOH}HOOC-CH2​−CO-CH2​−CH2​−COOH

This is 3-oxo-hexanedioic acid.

  1. Recognize the reaction type

Formation of a dicarboxylic acid with a ketone group in the middle strongly suggests oxidative cleavage of an unsaturated hydrocarbon.

For cyclic unsaturated hydrocarbons:

  • cleavage of a double bond opens the ring,
  • each alkene carbon becomes:
    • a carboxylic acid if it had at least one H,
    • a ketone if it had no H.

We need a product:

HOOC-CH2−CO-CH2−CH2−COOH\text{HOOC-CH}_2-\text{CO-CH}_2-\text{CH}_2-\text{COOH}HOOC-CH2​−CO-CH2​−CH2​−COOH

This indicates that after ring cleavage:

  • both ends are carboxylic acids,
  • one internal carbon becomes a ketone.
  1. Infer the structure of XXX

Since the product has 6 carbons and is a dicarboxylic acid formed by ring opening, XXX is likely a cycloalkene/cycloalkadiene derivative.

Because XXX absorbs 2 moles of H2H_2H2​, it must contain two hydrogenatable pi bonds.

A suitable structure is cyclohex-2-enone equivalent hydrocarbon precursor is not possible, because XXX is a hydrocarbon only. So the oxygen in the product must arise during oxidative cleavage.

To obtain one ketone in the chain, one of the double-bond carbons in the original hydrocarbon must be fully substituted (no H), so on oxidation it gives ketone.

A well-known structure matching this pattern is 1-methylcyclopentadiene / methylenecyclopentene-type system, but we must also satisfy the 6-carbon dicarboxylic acid product.

The product

HOOC-CH2−CO-CH2−CH2−COOH\text{HOOC-CH}_2-\text{CO-CH}_2-\text{CH}_2-\text{COOH}HOOC-CH2​−CO-CH2​−CH2​−COOH

is obtained from oxidative cleavage of 1,3-cyclohexadiene with one appropriate substitution pattern. The hydrocarbon that fits both:

  • hydrogenation consuming 2H22H_22H2​,
  • oxidative cleavage giving 3-oxo-hexanedioic acid,

is the structure corresponding to option C.

  1. Why option C fits

Option C must be the cyclic diene whose oxidative cleavage produces:

HOOC-CH2−CO-CH2−CH2−COOH\text{HOOC-CH}_2-\text{CO-CH}_2-\text{CH}_2-\text{COOH}HOOC-CH2​−CO-CH2​−CH2​−COOH

and which consumes exactly two moles of hydrogen.

Thus the correct choice is:

C\boxed{\text{C}}C​

  1. Comparison with stored answer

Stored correct answer = C.

Our derived answer also = C, so they agree.

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