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Organic Chemistry > Aldehyde & Ketone pt 2 > Flashcards

Aldehyde & Ketone pt 2 Flashcards

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1
Q

When choosing the parent chain of the aldehyde, have to identify the ________ chain that includes the carbon atom of the aldehyde group & the aldehyde gets higher priority over a substituent so its should have the lowest number

A

Longest

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2
Q

Aldehydes & ketones ae named using the same rules for naming _________

A

Alkanes

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3
Q

Aldehydes end with what?

A

“al” (ex. 3-methylpentanal)

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4
Q

Cyclic compound containing an aldehyde group adjacent to the ring is named as a ____________

A

Carbaldehyde (ex. cyclohexanecarbaldehyde)

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5
Q

What is the name of this simple aldehyde?

A

Formaldehyde

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6
Q

What is the name of this simple aldehyde?

A

Acetaldehyde

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7
Q

What is the name of this simple aldehyde?

A

Benzaldehyde

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8
Q

Ketones are named the using the same rules as ________

A

Alkanes

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9
Q

Ketones end in ______

A

“one” (ex. 3-methylpentanone)

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10
Q

What is the name of this simple ketone?

A

Acetone

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11
Q

What is the name of this simple ketone?

A

Acetophenone

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12
Q

What is the name of this simple ketone?

A

Benzophenone

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13
Q

Ketones can also be named as ____________ ketones

A

Alkyl Alkyl ketones (ex. ethyl propyl ketone)

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14
Q

Summary of past reaction used to make aldehydes

A
  1. Oxidation of primary alcohols
  2. Ozonolysis of alkenes
  3. Hydroboration-oxidation of terminal alkynes
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15
Q

Summary of past reaction used to make Ketones

A
  1. Oxidation of secondary alcohols
  2. Ozonolysis of alkenes
  3. Acid-catalyzed hydration of terminal alkynes
  4. Friedel craft acylation
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16
Q

A carbonyl group (c=o) is electrophilic because why?

A

It has both resonance & induction

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17
Q

Since in both resonance & induction the carbon connected to the double bond oxygen has a partial positive charge what does that mean?

A

Means its deficient in electron density which results to it becoming electrophilic

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18
Q

A carbonyl group is sp2 hybridized with what type of geometry?

A

Trigonal planar (120 degree bond angle)

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19
Q

Which is more reactive aldehyde or ketone & why?

A

Aldehydes are more reactive than ketone toward nucleophilic attack because of steric & electronic effect

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20
Q

Explain the steric effect aldehydes has over ketones

A

A ketone has two alkyl groups so in its transition state it basically is a secondary carbocation (which is pretty stable) but for aldehydes it has only one alkyl group so in its transition state is basically a primary carbocation which is unstable and why it’s more reactive

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21
Q

Explain the electronic effect that makes aldehydes more reactive than ketones

A

Alkyl groups like CH3 are electron donating so a ketone has two alkyl groups which stabilizes its partial charge but for aldehydes it only has one alkyl group so its partial charge isn’t stabilized

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22
Q

What is the mechanism for nucleophilic addition under basic condition?

A
  1. Nucleophilic attack
  2. Proton transfer
23
Q

What is the mechanism for nucleophilic attack under acidic condition?

A
  1. Proton transfer
  2. Nucleophilic attack
24
Q

Under nucleophilic attack on a carbonyl group the equilibrium position depends on the ability of what?

A

the nucleophile to function as a good leaving group

25
Q

________ are good nucleophiles & good leaving groups so when a ________ functions as a nucleophile the starting ketone is usually favored

A

Halide (so equilibrium favors the reactants)

26
Q

When an aldehyde or ketone is treated with water the carbonyl group can be converted into what?

A

Hydrate

27
Q

The position of equilibrium generally favors the _______ rather than the hydrate except in the case of using simple aldehydes like formaldehyde

A

Carbonyl group (reactants)

28
Q

What is the mechanism for base-catalyzed hydration formation?

A
  1. Nucleophilic attack
  2. Proton transfer
29
Q

What is the mechanism for acid-catalyzed hydration?

A
  1. Proton transfer
  2. Nucleophilic attack
  3. Proton transfer
30
Q

Under acidic conditions (H3O+) a mechanism will only be reasonable if it avoids the use or formation of a strong ___________ (only weak bases can be used)

A

Base

31
Q

Under basic condition a mechanism will only be reasonable if it avoids the use or formation of a strong _____________ (Only weak acids can be used)

A

Acid

32
Q

In acidic conditions (H3O+) an aldehyde or ketone will react with two molecules of alcohol (or 2 equivalents) to form an __________

A

Acetal

33
Q

When an aldehyde or ketone reacts with 1 equivalent of alcohol then it forms a _________

A

Hemiacetal

34
Q

What are some common acids used to form an acetal?

A
  1. TsOH
  2. Sulfuric acid (H2SO4)
35
Q

What is the mechanism for the formation of acetal?

A
  1. Proton transfer
  2. Nucleophilic attack
  3. Proton transfer
  4. (Hemiacetal is formed) (intermediate)
  5. Proton transfer
  6. Loss of leaving group
  7. Nucleophilic attack
  8. Proton transfer
  9. Acetal is formed (product)
36
Q

When forming acetals from simple aldehydes equilibrium favors the formation of the ___________

A

Acetal (Products) (Unless water is removed)

37
Q

Can covert acetals back into aldehydes or ketones with ________

A

Acidic Water (H3O+)

38
Q

Can use acetal group to _________ ketones or aldehydes

A

Protect

39
Q

When a compound contains both a carbonyl group & a hydroxyl group then a ___________ can be formed

A

Cyclic Hemiacetal

40
Q

When an aldehyde or ketone is treated with a primary ketone or NH3 it will form an _________

A

Imine (also called shiff bases)

41
Q

What is the mechanism for imine formation?

A
  1. Nucleophilic attack
  2. Proton Transfer
  3. Proton transfer
  4. Carbinolamine formed (intermediate)
  5. Proton transfer
  6. Loss of leaving
  7. Proton transfer
  8. Imine formed (product)
42
Q

When an aldehyde or ketone is treated with a secondary amine in acidic conditions it forms an ________

A

enamine

43
Q

Any aldehyde or ketone with an _________ treated with a secondary amine forms an enamine

A

Alpha protons (so no alpha protons no reaction)

44
Q

What is the mechanism for enamine formation?

A
  1. Nucleophilic attack
  2. Proton transfer
  3. Proton transfer
  4. Carbinolamine forms (intermediate)
  5. Proton transfer
  6. Loss of leaving
  7. Proton transfer
  8. Enamine form (product)
45
Q

Acetal can’t be turned back into ketones or aldehyde when treated with aqueous ________ conditions

A

Base (like NaOH/ H2O) (No reaction occurs)

46
Q

When aldehydes or ketones are treated with HCN or KCN/HCl they form __________

A

Cyanohydrin

47
Q

What is the mechanism for cyanohydrin formation?

A
  1. Nucleophilic attack
  2. Proton transfer
48
Q

Most equilibrium favors the formation of the ______

A

Cyanohydrin (Porducts)

49
Q

When a cyanohydrin is treated with LAH/H2O it ___________

A

It turns the CN into NH2 (so the compound has OH & NH2)

50
Q

When a cyanohydrin is treated with acidic water (H3O+) it _________

A

Turns the CN into a carboxylic acid (so the compound has OH & a carboxylic acid)

51
Q

A ___________ is the reagent used in a Wittig reaction

A

Phosphorous ylide (Wittig regent)

52
Q

What is the mechanism for a Wittig reaction?

A
  1. [2+2] Cycloaddition
  2. Fragmentation
53
Q

What is the mechanism for the formation of the Wittig reagent?

A

The mechanism involves an SN2 process followed by deprotonation with a strong base (so the phosphorous can’t be a tertiary compound)

Organic Chemistry (47 decks)

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