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Question
A compound 'A' of molecular formula C2H3OCl undergoes a series of reactions as shown below. Write the structures of A, B, C and D in the following reactions :
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Solution
Using the given molecular formula, compound A is Ethanoyl Chloride CH3COCl, which undergoes reaction with poisoned palladium.
On carrying hydrogenation of A in the presence of poisoned palladium, we get an aldehyde. Hence, B can be Ethanal, CH3CHO.
An aldehyde, on treating with dilute alkali, undergoes aldol condensation reaction. Hence, C can be CH3CH(OH)CH2CHO.
On heating an aldol product, it loses water to produce a double bond and we get CH3CH=CHCHO.
Hence, we have
RELATED QUESTIONS
Write the products formed when CH3CHO reacts with the following reagents: CH3CHO in the presence of dilute NaOH
What is meant by the following term? Give an example of the reaction in the following case.
Aldol
How will you convert ethanal into the following compound?
But-2-enal
Which of the following compounds do not undergo aldol condensation?
(i) \[\ce{CH3 - CHO}\]
(ii) 
(iii) \[\begin{array}{cc}
\phantom{}\ce{O}\\
\phantom{}||\\
\ce{CH3 - C - CH3}
\end{array}\]
(iv) \[\begin{array}{cc}
\phantom{}\ce{CH3}\\
|\phantom{...}\\
\ce{CH3 - C - CHO}\phantom{..}\\
|\phantom{...}\\
\phantom{}\ce{CH3}\\
\end{array}\]
Which of the following conversions can be carried out by Clemmensen Reduction?
(i) Benzaldehyde into benzyl alcohol
(ii) Cyclohexanone into cyclohexane
(iii) Benzoyl chloride into benzaldehyde
(iv) Benzophenone into diphenyl methane
Compound ‘A’ was prepared by oxidation of compound ‘B’ with alkaline \[\ce{KMnO4}\]. Compound ‘A’ on reduction with lithium aluminium hydride gets converted back to compound ‘B’. When compound ‘A’ is heated with compound B in the presence of \[\ce{H2SO4}\] it produces fruity smell of compound C to which family the compounds ‘A’, ‘B’ and ‘C’ belong to?
Assertion: The α-hydrogen atom in carbonyl compounds is less acidic.
Reason: The anion formed after the loss of α-hydrogen atom is resonance stabilised.
Give reasons to support the answer:
Presence of Alpha hydrogen in aldehydes and ketones is essential for aldol condensation.
Predict the reagent for carrying out the following transformations:
Ethanal to 3-hydroxy butanal
Which of the following does not give aldol condensation reaction?
