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Organic Chemistry > Aldehyde & Ketone > Flashcards

Aldehyde & Ketone Flashcards

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
A _______ acetal can be formed with the same mechanism for acetal formation
Cyclic
26
\_\_\_\_\_\_\_\_\_ can be used to protect ketones or aldehydes
Acetals
27
When a compound contains both a _________ & ________ group the resulting cyclic hemiacetal can be formed (isolated)
Carbonyl & OH group
28
In mildly acidic condition an aldehyde or ketone will react with a primary amine to form an \_\_\_\_\_\_
Imine (Shiff base)
29
What mechanism for imine formation?
1. Nucleophilic attack 2. Proton transfer 3. Carbinolamine (intermediate) 4. Proton transfer 5. Loss of LG 6. Proton transfer
30
Many different compounds of the form RNH2 will react with aldehydes or ketones where the R group can be an _____ or \_\_\_\_\_\_
OH or NH2
31
When hydroxylamine (NH2OH) is used as a nucleophile then an ________ is formed
Oxime
32
When hydrazine (NH2NH2) is used as a nucleophile a ___________ is formed
Hydrazone
33
Both the formation of oxime & hydrazone have the same mechanism as the formation of an \_\_\_\_\_\_\_
Imine
34
In acidic conditions, an aldehyde or ketone will react with a secondary amine to form an \_\_\_\_\_\_\_\_\_
Enamine
35
What is the mechanism for the formation of enamine?
1. Nucleophile attack 2. Proton transfer 3. Carbinolamine 4. Proton transfer 5. Loss of LG 6. Proton transfer
36
Wolff-Kisher reduction
Reduces a hydrazone into an alkane with KOH/H2O & heat
37
What is the mechanism for the wolf-kishner reduction?
1. Proton transfer 2. Proton transfer 3. Proton transfer 4. Loss of LG 5. Proton transfer
38
In a __________ reaction bonds are cleaved when treated with water
Hydrolysis
39
What is the mechanism for a hydrolysis of acetals?
1. Proton transfer 2. Loss of LG 3. Proton transfer 4. Hemiacetal 5. Proton transfer 6. Loss of LG 7. Proton transfer
40
In acidic conditions an aldehyde or ketone will react with 2 equivalents of thiol to form a \_\_\_\_\_\_\_\_\_\_
Thioacetal
41
The formation of thioacetal has the same mechanism as the formation of \_\_\_\_\_\_\_\_\_
Acetal
42
If a compound with two SH group is used then a cyclic ___________ is formed
thioacetal
43
When treated with _________ thioacetals undergo desulfurization yielding an alkane
Raney Nickel
44
Can reduce ketones with _________ & __________ to form alkanes
Thioacetals & Raney Ni
45
Ketones & aldehydes can be reduced to alcohols by ________ reducing agents like LAH & NaBH4
Hydride
46
What is the mechanism for reduction of ketone or aldehydes with hydride reagents?
1. Nucleophilic attack 2. Proton transfer
47
When treated with __________ aldehydes or ketones care converted into alcohols
Grignard reagent
48
When treated with hydrogen cyanide (HCN) aldehydes or ketones are converted into \_\_\_\_\_\_\_\_\_\_\_
Cyanohydrins
49
What is mechanism for cyanohydrin formation?
1. Nucleophilic attack 2. Proton Transfer
50
\_\_\_\_\_\_\_\_\_\_\_\_\_\_ can also be formed by treating a ketone or aldehyde with potassium cyanide & HCl (or another source of protons)
Cyanohydrins
51
Wittig Reaction
Converts a ketone into alkene
52
A ________________ is used to convert a ketone to an alkene
Phosphorus ylide (Wittig reagent)
53
What is the mechanism for the Wittig reaction?
1. [2+2] cycloaddition 2. Fragmentation
54
\_\_\_\_\_\_\_\_\_\_\_\_\_ 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
Wittig Reagent
55
Baeyer Villiger reaction
When treated with peroxy acids ketones can be converted into ester by insertion of an oxygen atom
56
What is the mechanism for the Beayer Villiger oxidation?
1. Nucleophilic attack 2. Proton transfer 3. Rearrangement
57
When a cyclic ketone is treated with peroxy acid the product is \_\_\_\_\_\_\_\_\_\_\_
Cyclic ester (lactone)
58
When unsymmetrical ketone is treated with peroxy acid formation is ester is \_\_\_\_\_\_\_\_\_\_\_\_
Regioselective
59
Migratory aptitude (migration rates) is what?
H\>3o\>20, Ph\>10\>methyl (increasing order so H migrates most rapidly)
60
What ae the 4 reaction that change the carbon skeleton?
1. Grignard reaction 2. Cyanohydrin formation 3. Wittig reaction 4. Baeyer Villiger oxidation
61
Carbonyl groups produces a strong signal in IR spectrum around ________ or \_\_\_\_\_\_\_\_
1715 or 1720cm-1
62
A ____________ carbonyl group will produce a signal at a lower wavenumber
conjugated
63
When you increase the ring strain then the wavenumber \_\_\_\_\_\_\_\_\_\_
Increases
64
Aldehydes usually have one or 2 signals between ______ & \_\_\_\_\_cm-1
2700 & 2850cm-1
65
Carbonyl groups adds ____ to the chemical shift of its neighbors
+1
66
Aldehydes proton usually produce signals around _____ ppm
10 ppm
67
In a 13C spectrum the carbonyl group of a ketone or aldehyde will have a weak signal near ________ ppm
200ppm
68
Can hydrolyze an acetal, imine, enime with acidic aqueous water to form a \_\_\_\_\_\_\_\_\_
Ketone
69
When Acetal is treated with Acidic water it can be converted back into a \_\_\_\_\_\_\_\_\_\_
Ketone
70
Can turn a ketone carbonyl group into an ___________ for protection
Acetal
71
A cyanohydrin can be reduced with LAH to produce \_\_\_\_\_\_\_\_\_\_\_\_
A compound with OH & NH2
72
Cyanohydrins can be reduced with Acidic water & heat to produce \_\_\_\_\_\_\_\_\_\_\_
OH & carboxylic acid

Organic Chemistry (47 decks)

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