Carbonyls Flashcards

0
Q

How is the Cyanide Ion formed?

A

By Heterolytic Fission of HCN forming H+ and NC:-

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1
Q

What is formed when HCN is added to a Carbonyl?

A

A Hydroxy Nitrile that has gained an extra Carbon

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2
Q

Define Heterolytic Fission

A

The breaking of a bond in which the two fragments result in having opposite charges

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3
Q

Show a Hydroxy Nitrile being formed from a Carbonyl

A

Key:
R=Carbon Chain or Hydrogen
——-
2 R groups attached to a C and a O double bonded to the C. The C has a delta+ and the O a delta-
NC- curvy arrow to the delta+ C from opposite the delta- O
And curvy arrow from the bond between the delta- O and delta+ C to the delta- O
Over the arrow——–
NC-C-O (O has - sign) (C still has two R groups)
Curvy arrow from O- to H+
Over the arrow ——-
NC-C-OH (2R groups still on C)

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4
Q

Draw Hydrogen Cyanide reacting with a Carbonyl

A

Key:
R=Carbon Chain or Hydrogen
——-
2 R groups attached to a C and a O double bonded to the C. The C has a delta+ and the O a delta-
NC- curvy arrow to the delta+ C from opposite the delta- O
And curvy arrow from the bond between the delta- O and delta+ C to the delta- O
Over the arrow——–
NC-C-O (O has - sign) (C still has two R groups)
Curvy arrow from O- to H+
Over the arrow ——-
NC-C-OH (2R groups still on C)

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5
Q

What type of reaction occurs when HCN is added to a Carbonyl?

A
Nucleophilic Addition
(The C=O becomes saturated)
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6
Q

How are carbonyls attractive to nucleophiles?

A

The asymmetric electron distribution forms a Cδ+

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7
Q

Why are aldehydes more attractive to nucleophiles than ketones?

A

H is more approachable than a tetrahedral CH3

Alkyl groups allow drift of electrons (making C less δ+ )

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8
Q

What hydrogen bonding occurs with carbonyls?

A

Carbonyl- water H bonding occurs due to the Oδ-

Intermolecular doesn’t

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9
Q

What feature of carbonyls makes them soluble in water?

A

Their ability to H bond with water

(Carbonyl’s Oδ- — water’s Hδ+

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