Carbonyl Reactions

Chemistry Level 4

When 3-Hydroxy Butanal is heated with aqueous $\ce{NaOH}$ , a compound with molecular weight $M$ is formed.

Find $M$ .

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The answer is 70.

1 solution

Ronak Agarwal
Apr 22, 2015

Acetaldehyde is formed.

Retro aldol reaction

why so ? why we can't do aldol ? Also I think Retro aldol is occure when compound is alpha hydroxy Ketone or aldehyde .... But in this question it is Beeta hydroxy aldehyde ... ?

Karan Shekhawat - 6 years, 1 month ago

Think again whether it must be alpha or beta hydroxy aldehyde.

Remember aldol reaction is reversible reaction and hence retro aldol takes place.

Don't worry this problem is all right.

Ronak Agarwal - 6 years, 1 month ago

why cant we just dehydrate the product isnt retro aldol favoured when the ketone is sterically hindered please explain it to me

Siddhartha Biswas - 5 years, 6 months ago

ohh yes... sorry ! I got it..! Tricky Question ... :)

Karan Shekhawat - 6 years, 1 month ago

Ronak, can you please tell what is retro aldol .

Karan Siwach - 6 years, 1 month ago

@Karan Siwach – Reversible Aldol reaction.

Ronak Agarwal - 6 years, 1 month ago

@Ronak Agarwal – Hey I got like this.In Basic medium Keto exists in the form of enolaten so A conjugating structure of this is possible in which the 2nd(as per nomenclature) carbon of the carbonyl group gets a negative charge.Now as we are heating we can expect elimination (E1CB).The negative pushes the OH to depart thus leading to a double bond.The Mass is 70.

Spandan Senapati - 4 years, 1 month ago

http://www.chem.uky.edu/courses/che232/JEA/ln/7.%20Carbonyl%20Condensats.pdf

Mvs Saketh - 6 years, 1 month ago

Carbonyl Reactions

Image Credit: Wikimedia Ring0 .

The answer is 70.

1 solution

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