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Topic 17: Organic Chemistry II
17.1 Carbonyl Compounds
17.1.2 Reactions of Carbonyl Compounds
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What is the functional group in carbonyl compounds?
C=O
Aldehydes have the general formula
RCHO
Aldehydes must have at least one hydrogen atom bonded to the
carbonyl group
.
What is the general formula for ketones?
RCOR'
Carbonyl compounds are polar due to the electronegativity difference between carbon and
oxygen
Carbonyl compounds have high reactivity due to the
C=O
bond.
Which type of carbonyl compound is readily oxidized to carboxylic acids?
Aldehydes
Match the carbonyl compound with its example:
Aldehydes ↔️ Methanal (
H
C
H
O
HCHO
H
C
H
O
)
Ketones ↔️ Propanone (
C
H
3
C
O
C
H
3
CH_{3}COCH_{3}
C
H
3
COC
H
3
)
What type of reaction involves a nucleophile attacking the carbonyl carbon?
Nucleophilic addition
In nucleophilic addition, the carbonyl double bond breaks to form a single bond with the
nucleophile
.
Aldehydes are more reactive than ketones in nucleophilic addition due to less steric
hindrance
What type of product is formed when aldehydes and ketones are hydrated?
Gem-diols
Hydration of carbonyl compounds requires either acid or
base catalysts
.
Steps in the hydration mechanism of carbonyl compounds
1️⃣ Activation of carbonyl group
2️⃣ Nucleophilic attack by water
3️⃣ Proton transfer
The hydration of acetaldehyde in an acidic environment forms
gem-diols
What type of product is formed when aldehydes and ketones are hydrated?
Gem-diols
What type of product is formed when aldehydes and ketones undergo hydration?
Gem-diols
Protonation or deprotonation of the carbonyl group in aldehydes and ketones enhances its electrophilicity or
nucleophilicity
.
Arrange the steps in the mechanism of aldehyde and ketone hydration.
1️⃣ Activation of Carbonyl Group
2️⃣ Nucleophilic Attack by Water
3️⃣ Proton Transfer
In the hydration of aldehydes and ketones, water attacks the carbonyl
carbon
What is formed when aldehydes and ketones react with hydrogen cyanide (HCN)?
Cyanohydrins
The cyanide ion acts as a
nucleophile
in the formation of cyanohydrins.
In the final step of cyanohydrin formation, the oxygen ion picks up a
proton
Arrange the steps in the reaction of Grignard reagents with aldehydes and ketones.
1️⃣ Nucleophilic Attack by R⁻
2️⃣ Magnesium Alkoxide Formation
3️⃣ Hydrolysis
Anhydrous conditions are essential for reactions involving
Grignard reagents
to ensure safety.
What is the functional group in carbonyl compounds?
\chem{C = O}
Match the type of carbonyl compound with its general formula.
Aldehydes ↔️
R
C
H
O
RCHO
RC
H
O
Ketones ↔️
R
C
O
R
′
RCOR'
RCO
R
′
Carbonyl compounds are polar due to the electronegativity difference between carbon and
oxygen
Ketones are readily oxidized to carboxylic acids.
False
What type of bond is broken in nucleophilic addition reactions with carbonyl compounds?
\chem{C = O}
Arrange the steps in the mechanism of nucleophilic addition reactions with carbonyl compounds.
1️⃣ Nucleophilic Attack
2️⃣ Protonation
Aldehydes are more reactive than ketones in nucleophilic addition reactions due to less
steric
hindrance.
What is the final product of aldehyde and ketone hydration?
Gem-diols
Why are aldehydes more reactive than ketones?
Less steric hindrance
Aldehydes react with HCN to form
cyanohydrins
Nucleophilic addition reactions involve the nucleophile attacking the
carbonyl
carbon.
Steps in the mechanism of a nucleophilic addition reaction
1️⃣ Nucleophilic Attack
2️⃣ Protonation
What makes aldehydes more reactive than ketones in nucleophilic addition reactions?
Less steric hindrance
Hydration of aldehydes and ketones requires an acid or base
catalyst
Gem-diols have two OH groups attached to the same
carbon
atom.
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