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Organic Chemistry > Aldehyde & Ketone > Flashcards

Aldehyde & Ketone Flashcards

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1
Q

Aldehyde & ketones both have a ________ group

A

Carbonyl

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2
Q

Aldehydes & ketones are named the same way as _________

A

Alkanes (same rules)

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3
Q

When choosing the parent of an aldehyde have to identify the longest chain that includes the carbon atom of the ____________ group

A

Aldehyde group

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4
Q

Aldehyde ends in _____

A

“al”

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5
Q

When numbering an aldehyde has ______ priority over any substituents even over an OH group
so should have the lowest #

A

Higher

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6
Q

Cyclic compounds with aldehydes group directly adjacent to the ring end in ____________

A

“Carbaldehyde” ex. Cylcohexanecarbaldehyde

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7
Q

What is the name of this simple aldehyde ?

A

Formaldehyde

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8
Q

What is the name of this simple aldehyde ?

A

Acetaldehyde

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9
Q

What is the name of this simple aldehyde ?

A

Benzaldehyde

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10
Q

Ketones end in what?

A

“one” ex. Butanone

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11
Q

What is the name of this simple ketone?

A

Acetone

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12
Q

What is the name of this simple ketone?

A

Acetophenone

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13
Q

What is the name of this simple ketone?

A

Benzophenone

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14
Q

What is the mechanism for nucleophilic addition under basic conditions for ketones & aldehydes?

A
  1. Nucleophilic attack
  2. Proton transfer
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15
Q

What is the mechanism for nucleophilic addition under acidic conditions?

A
  1. Proton transfer
  2. Nucleophilic attack
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16
Q

When an aldehyde or ketone is treated with water, the carbonyl groups can be converted into a _________

A

Hydrate

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17
Q

The position of equilibrium generally favors the _________ rather than the hydrate except when dealing with simple aldehydes like formaldehyde

A

Carbonyl

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18
Q

What is the mechanism for basic catalyzed hydration?

A
  1. Nucleophilic attack
  2. Proton transfer
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19
Q

What is mechanism for acid catalyzed hydration?

A
  1. Proton transfer
  2. Nucleophilic attack
  3. Proton transfer
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20
Q

Under _______ conditions a mechanism will only be reasonable if it avoids the use or formation of strong base (only weak bases can be employed)

A

Acidic

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21
Q

Under ______ condition a mechanism will only be reasonable if it avoids the use or formation of strong acid (only weak acids can be employed)

A

Basic

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22
Q

In ______ conditions an aldehyde or ketone will react with two molecules of alcohols to form an acetal

A

Acidic

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23
Q

What are the two common acids use for the reaction to convert a ketone or aldehyde into an acetal?

A
  1. p-Toluenesulfonic acid (TsOH)
  2. Sulfonic acid (H2SO4)
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24
Q

What is the mechanism for acetal formation?

A
  1. Proton transfer
  2. Nucleophilic attack
  3. Proton transfer
  4. Hemiacetal (intermediate)
  5. Proton transfer
  6. Loss of LG
  7. Nucleophilic attack
  8. Proton transfer
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25
Q

A _______ acetal can be formed with the same mechanism for acetal formation

A

Cyclic

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26
Q

_________ can be used to protect ketones or aldehydes

A

Acetals

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27
Q

When a compound contains both a _________ & ________ group the resulting cyclic hemiacetal can be formed (isolated)

A

Carbonyl & OH group

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28
Q

In mildly acidic condition an aldehyde or ketone will react with a primary amine to form an ______

A

Imine (Shiff base)

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29
Q

What mechanism for imine formation?

A
  1. Nucleophilic attack
  2. Proton transfer
  3. Carbinolamine (intermediate)
  4. Proton transfer
  5. Loss of LG
  6. Proton transfer
30
Q

Many different compounds of the form RNH2 will react with aldehydes or ketones where the R group can be an _____ or ______

A

OH or NH2

31
Q

When hydroxylamine (NH2OH) is used as a nucleophile then an ________ is formed

A

Oxime

32
Q

When hydrazine (NH2NH2) is used as a nucleophile a ___________ is formed

A

Hydrazone

33
Q

Both the formation of oxime & hydrazone have the same mechanism as the formation of an _______

A

Imine

34
Q

In acidic conditions, an aldehyde or ketone will react with a secondary amine to form an _________

A

Enamine

35
Q

What is the mechanism for the formation of enamine?

A
  1. Nucleophile attack
  2. Proton transfer
  3. Carbinolamine
  4. Proton transfer
  5. Loss of LG
  6. Proton transfer
36
Q

Wolff-Kisher reduction

A

Reduces a hydrazone into an alkane with KOH/H2O & heat

37
Q

What is the mechanism for the wolf-kishner reduction?

A
  1. Proton transfer
  2. Proton transfer
  3. Proton transfer
  4. Loss of LG
  5. Proton transfer
38
Q

In a __________ reaction bonds are cleaved when treated with water

A

Hydrolysis

39
Q

What is the mechanism for a hydrolysis of acetals?

A
  1. Proton transfer
  2. Loss of LG
  3. Proton transfer
  4. Hemiacetal
  5. Proton transfer
  6. Loss of LG
  7. Proton transfer
40
Q

In acidic conditions an aldehyde or ketone will react with 2 equivalents of thiol to form a __________

A

Thioacetal

41
Q

The formation of thioacetal has the same mechanism as the formation of _________

A

Acetal

42
Q

If a compound with two SH group is used then a cyclic ___________ is formed

A

thioacetal

43
Q

When treated with _________ thioacetals undergo desulfurization yielding an alkane

A

Raney Nickel

44
Q

Can reduce ketones with _________ & __________ to form alkanes

A

Thioacetals & Raney Ni

45
Q

Ketones & aldehydes can be reduced to alcohols by ________ reducing agents like LAH & NaBH4

A

Hydride

46
Q

What is the mechanism for reduction of ketone or aldehydes with hydride reagents?

A
  1. Nucleophilic attack
  2. Proton transfer
47
Q

When treated with __________ aldehydes or ketones care converted into alcohols

A

Grignard reagent

48
Q

When treated with hydrogen cyanide (HCN) aldehydes or ketones are converted into ___________

A

Cyanohydrins

49
Q

What is mechanism for cyanohydrin formation?

A
  1. Nucleophilic attack
  2. Proton Transfer
50
Q

______________ can also be formed by treating a ketone or aldehyde with potassium cyanide & HCl (or another source of protons)

A

Cyanohydrins

51
Q

Wittig Reaction

A

Converts a ketone into alkene

52
Q

A ________________ is used to convert a ketone to an alkene

A

Phosphorus ylide (Wittig reagent)

53
Q

What is the mechanism for the Wittig reaction?

A
  1. [2+2] cycloaddition
  2. Fragmentation
54
Q

_____________ is prepared by treating triphenylphosphine with an alkyl halide followed by a strong base in an SN2 reaction followed by deprotonation with the strong base

A

Wittig Reagent

55
Q

Baeyer Villiger reaction

A

When treated with peroxy acids ketones can be converted into ester by insertion of an oxygen atom

56
Q

What is the mechanism for the Beayer Villiger oxidation?

A
  1. Nucleophilic attack
  2. Proton transfer
  3. Rearrangement
57
Q

When a cyclic ketone is treated with peroxy acid the product is ___________

A

Cyclic ester (lactone)

58
Q

When unsymmetrical ketone is treated with peroxy acid formation is ester is ____________

A

Regioselective

59
Q

Migratory aptitude (migration rates) is what?

A

H>3o>20, Ph>10>methyl (increasing order so H migrates most rapidly)

60
Q

What ae the 4 reaction that change the carbon skeleton?

A
  1. Grignard reaction
  2. Cyanohydrin formation
  3. Wittig reaction
  4. Baeyer Villiger oxidation
61
Q

Carbonyl groups produces a strong signal in IR spectrum around ________ or ________

A

1715 or 1720cm-1

62
Q

A ____________ carbonyl group will produce a signal at a lower wavenumber

A

conjugated

63
Q

When you increase the ring strain then the wavenumber __________

A

Increases

64
Q

Aldehydes usually have one or 2 signals between ______ & _____cm-1

A

2700 & 2850cm-1

65
Q

Carbonyl groups adds ____ to the chemical shift of its neighbors

A

+1

66
Q

Aldehydes proton usually produce signals around _____ ppm

A

10 ppm

67
Q

In a 13C spectrum the carbonyl group of a ketone or aldehyde will have a weak signal near ________ ppm

A

200ppm

68
Q

Can hydrolyze an acetal, imine, enime with acidic aqueous water to form a _________

A

Ketone

69
Q

When Acetal is treated with Acidic water it can be converted back into a __________

A

Ketone

70
Q

Can turn a ketone carbonyl group into an ___________ for protection

A

Acetal

71
Q

A cyanohydrin can be reduced with LAH to produce ____________

A

A compound with OH & NH2

72
Q

Cyanohydrins can be reduced with Acidic water & heat to produce ___________

A

OH & carboxylic acid

Organic Chemistry (47 decks)

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