Back to marketplace

Nucleophilic substitution with loss of carbonyl oxygen

No description yet. This curated deck is ready for daily study.

Total cards: 23•Content version: v4•Public deck•Updated: 8/1/2026

Card preview (23)

#1
Front (Question)

Draw the mechanism for the nucleophilic substitution with loss of carbonyl

Back (Answer)

-

#2
Front (Question)

How do you make something a better leaving group?

Back (Answer)

Protonate it

#3
Front (Question)

What is Keq for aldehydes? Is this favourable or unfavourable?

Back (Answer)

0.01 Unfavourable

#4
Front (Question)

What is the overall equation for acetal formation and how can this reaction become more favourable?

Back (Answer)

Aldehyde + 2ROH acetal + H2O Remove water as it formed to drive eq to the RHS

#5
Front (Question)

Why is Keq so low for acetal formation?

Back (Answer)

Both entropically and enthalpically unfavourable

#6
Front (Question)

How is acetal formation entropically unfavourable?

Back (Answer)

From 3 molecules to 2 molecules

#7
Front (Question)

Why do the entropy and enthalpy factors affect Keq?

Back (Answer)

They cause ΔG to be positive which is not favourable

#8
Front (Question)

Which conditions are acetals hydrolysed under?

Back (Answer)

Acidic H+ , H2O

#9
Front (Question)

What are acetals stable to?

Back (Answer)

Base hydrolysis HO-, H2O

#10
Front (Question)

Why is it good to convert an aldehyde to an acetal?

Back (Answer)

Acetal acts as a protecting group

#11
Front (Question)

What is an imine?

Back (Answer)

Nitrogen equivalent of a carbonyl compound

#12
Front (Question)

What does imine formation require?

Back (Answer)

acid catalysis

#13
Front (Question)

How does an imine compare to amine and ketone?

Back (Answer)

Unstable Keq < 1

#14
Front (Question)

How can equilibrium be driven to form the imine?

Back (Answer)

Remove water as it is formed

#15
Front (Question)

What reaction are imines involved in? How are they involved?

Back (Answer)

Reduction of amides through a double hydride addition There is an iminium ion intermediate

#16
Front (Question)

What reagent is required for the reduction of amides?

Back (Answer)

LiAlH4

#17
Front (Question)

What is the Wittig reaction?

Back (Answer)

Substitution of C=O for C=C

#18
Front (Question)

What is a ylide?

Back (Answer)

Molecule with adjacent positive and negative charges

#19
Front (Question)

What reagent is involved in the Wittig reaction?

Back (Answer)

Ph3P–CH2

#20
Front (Question)

Which bit of the reagent is swapped out in the Wittig reagent? What for?

Back (Answer)

-CH2 for =O

#21
Front (Question)

What is a ylid?

Back (Answer)

Molecule with adjacent positive and negative charges

#22
Front (Question)

What is the driving force for the Wittig reaction?

Back (Answer)

P=O bond strength as it is extremely strong which creates an irreversible reaction

#23
Front (Question)

How is a phosphonium ylid formed?

Back (Answer)

Using Me - I to form a phosphonium salt and then a strong base