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MCAT Organic > Aldehydes & Ketones > Flashcards

Aldehydes & Ketones Flashcards

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MCAT flashcards
1
Q

Suffix on aldehydes

A

-al

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2
Q

What prefix is used when aldehydes are substituents

A

oxo-

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3
Q

What suffix is used if the aldehyde is attached to a ring?

A

-carbaldehyde

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4
Q

What suffix is used for ketones

A

-one

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5
Q

What kind of bonding can aldehydes & ketones go though?

A

Dipole-dipole interactions

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6
Q

What kind of reactant are aldehydes & ketones?

A

electrophiles

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7
Q

Which are more polar, aldehydes/ketones or alcohols?

A

Aldehydes/ketones

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8
Q

Nucleophilic Addition

A

Nucleophile attacks & opens carbonyl, if there is a good leaving group, the carbonyl can reform

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9
Q

What can aldehydes & ketones form in the presence of water?

A

Geminal diols (1,1 / On the same carbon)

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10
Q

What is the geminal diol formation called?

A

Hydration

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11
Q

What is the nucleophile in hemiacetal/hemiketal formation?

A

1 equi of alcohol

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12
Q

What is a hemiacetal/hemiketal

A

Formation of alcohol & acid from aledhyde/ketone

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13
Q

What nucleophile is used for acetal/ketal formation?

A

2 equiv of alcohol

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14
Q

What kind of reaction produces acetal/ketal

A

SN1

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15
Q

Imine

A

A compound with a nitrogen atom double-bonded to a carbon atom

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16
Q

What kind of reaction is imine formatiosonance n?

A

Condensation/Nucleophilic substitution

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17
Q

What are common ammonia derivatives that react with aldehyde & ketones

A

Hydroxylamine, hydrazine, semicarbazide

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18
Q

Enamines

A

Imines that undergo tautomerization (Double bond & a nitrogen-containing group

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19
Q

Cyanohydrins

A

Reactions with aldehydes & ketones with hydrogen cyanide

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20
Q

Can ketones form carboxylic acids?

A

NO

21
Q

Reducing agents for ketones & aldehydes

A

LiAlH4 & NaBH4

22
Q

a-carbon

A

Adjacent to carbonyl carbon & hydrogens connected to them are a-hydrogens

23
Q

Why are a-hydrogens so acidic?

A

Resonance stability of conjugate base

When hydrogen is removed, extra electons can resonate between a-carbon, carbonyl , carbonyl oxygen

24
Q

Carbanion

A

Negatively charged carbon atom that is helped to stabilize by electron-withdrawing oxygen

25
Q

Which alpha protons are more acidic, aldehydre or ketone?

A

Aldehyde (ketone has electron donating groups)

26
Q

What does the additional alkyl groups on the ketone cause?

A

Steric hindrance

27
Q

How do aldehydes & ketones exist in a solution?

A

Mixture of keto & enol forms due to the acidity of a- hydrogens

28
Q

Enol form

A

Carbon-carbon double bond & alcohol component

29
Q

Tautomers

A

Keto & enol forms that differ in placement of proton & double bond

30
Q

Enolization/tautomerization

A

Process of interconverting from keto-enol foms

31
Q

Which tautomer is thermodynamically favored?

A

Keto form

32
Q

a-racemization

A

Aldehyde or ketone with chiral a-carbon will rapidly become a racemic mixture as the forms interconvert

33
Q

What are common strong bases?

A

OH-, lithium disopropyl amide (LDA), Potassium hydride (KH)

34
Q

What can deprotonated enols be used as?

A

Nucleophiles if treated with strong base first

35
Q

Michael addition

A

Carbanion of dicarbonyl attacks an a,B-unsaturated carbonyl compound of a dicarbonyl

36
Q

Thermodynamic enolate

A

One connected to more substituted carbon

37
Q

Kinetic enolate

A

One connected to less substituted carbon

38
Q

Which product is favored in fast & irresversible?

A

Kinetic

39
Q

Which product is favored at low temperature?

A

Kinetic

40
Q

Which product is favored with strong, sterically hindered base?

A

Kinetic

41
Q

When is the thermodynamic product favored?

A

Slow, reversible, weaker & smaller bases

42
Q

Enamine

A

CC double bond attached to a amine

43
Q

Which is thermodynamically favored enamine or imine?

A

Imine

44
Q

Aldol condensation

A

Aldehyde/ketone acts as both an electrophile (keto form) and nucleophile (in enolate from)
Ends in formation of CC bond

45
Q

Aldol

A

A carbonyl and OH groups combined bc of a combination of two acetaldehyde molecules with the enolate form attacking another carbonyl to form the alcohol group

46
Q

Dehydration of the aldol

A

Strong base & high temps will kick off a water molecule & form a double bond (E1 & E2) to make an a,B unsaturated

47
Q

What helps to specifically bind to one reactant?

A

Attack aldehyde or ketone that has no a-hydrogens (quatenary a-carbons like benzyladehyde)

48
Q

Retro aldol reaction

A

Aqueous base & heat to get back to aldehyde or ketone form

MCAT Organic (10 decks)

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