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Nucleophilic addition reactions
Appears in
Concepts tested here
- Addition-elimination with ammonia derivatives
- Addition–elimination with ammonia derivatives
- Ketal formation
- Reactivity of carbonyl compounds
All Questions
2015 AIPMT-II 1 question
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Reaction of carbonyl compound with one of the following reagents involves nucleophilic addition followed by elimination of water. The reagent is:Carbonyl compounds react with ammonia derivatives such as hydrazine (in feebly acidic medium) by nucleophilic addition followed by elimination of water, giving hydrazones.
2014 AIPMT 1 question
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Which one is most reactive towards Nucleophilic addition reaction?Reactivity towards nucleophilic addition depends on steric and electronic effects.
Order: p-nitrobenzaldehyde > benzaldehyde > p-tolualdehyde > acetophenone
The –M effect of $-NO_2$ increases the positive charge on the $sp^2$ carbonyl carbon.
2012 AIPMT-MAINS 1 question
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Consider the reaction: $RCHO + NH_2NH_2 \rightarrow RCH=N-NH_2$. What sort of reaction is it?Hydrazine has a lone pair on nitrogen and acts as a nucleophile.
Step 1 (nucleophilic addition): $NH_2NH_2$ attacks the carbonyl carbon of RCHO to give $RCH(OH)-NH-NH_2$.
Step 2 (elimination): a molecule of water is lost to give the hydrazone $RCH=N-NH_2$.
So it is a nucleophilic addition–elimination reaction.
2012 AIPMT-PRE 1 question
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Acetone is treated with excess of ethanol in the presence of hydrochloric acid. The product obtained is:In the presence of dry HCl, one molecule of ethanol adds to the carbonyl group of acetone to give a hemiketal, $(CH_3)_2C(OH)(OC_2H_5)$.
With excess ethanol the hemiketal reacts with a second molecule of ethanol, losing water, to give the ketal.
$(CH_3)_2C=O + 2C_2H_5OH \xrightarrow{HCl} (CH_3)_2C(OC_2H_5)_2 + H_2O$
So the product is 2,2-diethoxypropane, $(CH_3)_2C(OC_2H_5)_2$.
