What is the major organic product of aldol condensation of propanal? Type its sy
ID: 606692 • Letter: W
Question
What is the major organic product of aldol condensation of propanal? Type its systematic IUPAC name in the box below (don't indicate stereochemistry of the double bond in your name).Explanation / Answer
aldol condensation is based on the acidity of alpha hydrogens of aldehydes.... the carbon atom next to carbonyl group is called is called alpha carbon and the hydrogens attached are called alpha hydrogens....due to electron-withdrawing inductive effect of carbonyl group ,it withdraws electron from adjacent carbon-carbon bond...this makes alpha carbon electron deficient.....the alpha carbon in turns withdraw electron from the bond in between alpha carbon and hydrogen atoom i.e. alpha carbon-H bond ...as a result electron density in alpha carbon-H bond decreases ....in other words alpha hydrogens are quite weakly held and hence can be easily abstracted by strong bases giving enolate. anions which are stabilized by resonance.. thus the acidity of alpha hydrogens is due to the -I effect of carbonyl group which weakens the bond in between alpha carbon-H bond and partly due to resonance stabilization of resulting enolate anion.. in this reaction two molecules of an aldehyde condense in presence of dilute alkali..to form a beta-hydroxyaldehyde...these beta-hydroxyaldehydes are known as aldols... the name aldol (ald stands for -aldehyde and ol- stands for alcohol) is derived from the names of two functional groups aldehydes and alcohols ,present in product of condensation of two molecules of an aldehyde .... only one product will be formed in this case as it is confined to the condensation of two molecules of same aldehyde..... propanal + Dil.NaOH --------> 3-hydroxy-2-methyl-pentanal (an aldol) two molecules of propanal condense in presence of dil.NaOH gives this as the only product... more than one product is formed when you use two or more than two different kinds of aldehydes....in that case also it is difficult to tell which aldol is the major product and hence it has low synthetic value...
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