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Organic Chemistry 2 > Chapter 19- Aldehydes and Ketones > Flashcards

Chapter 19- Aldehydes and Ketones Flashcards

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1
Q

What is the suffix for ketones?

A

-one

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2
Q

What is the suffix for aldehydes?

A

-al

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3
Q

What is the IR signal for a ketone?

A

~1715 cm -1

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4
Q

What is the IR signal for an Aldehyde?

A

A weak 2700-2800 C-H stretch

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5
Q

How do you turn a Primary ROH into an aldehyde?

A

PCC, CH2Cl2
or
DMP, CH2Cl2
or
1) DMSO (COCl2)
2) Et2

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6
Q

How do you create an aldehyde from an RH=RH (alkene)?

A

Ozonolysis-
1) O3
2) DMS

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7
Q

How do you create a ketone from an alkene?

A

Ozonolysis-
1) O3
2) DMS

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8
Q

How do you create an aldehyde from an alkyne?

A

Hydroboration oxidation-

1) R2B-H
2)H202, NaOH

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9
Q

How do you create a ketone from an alkyne?

A

Acid Hydration-

H2SO4, H2O
HgSO4

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10
Q

Name this molecule

A

Formaldehyde

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11
Q

Name this molecule

A

Acetaldehyde

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12
Q

Name this molecule

A

Benzaldehyde

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13
Q

How do you make a ketone from a secondary alcohol?

A

Oxidation reaction with

Na2Cr2O7
H2SO4, H2O

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14
Q

How do you synthesize a ketone attached to a benzene ring from a benzene ring?

A

Friedel-Crafts acylation

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15
Q

How do you synthesize an aldehyde attached to a benzene ring from a benzene ring?

A

Gattermann-Koch formylation
CO, HCl

AlCl3/CuCl

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16
Q

Describe the carbon of the carbonyl within the aldehyde/ketone

A

-Electrophilic
-Has a delta plus from Induction
-Attacked by nucleophiles

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17
Q

match the strength of the nucleophiles to the type to conditions and if it is reversible or not

A

Weak Nucleophile, Acid Conditions, Reversible

Strong nucleophile, base conditions, irreversible.

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18
Q

What is more reactive? Aldehydes or Ketones?

why?

A

Aldehydes are more reactive:
1. Less sterically hindered
2. Only has one electron donating alkyl group, a delta plus on the carbonyl carbon

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19
Q

How do you turn a ketone into a Secondary Alcohol? (Hydride strong nucleophile reagent)

A

1)LAH
2)H2O

or

NaBH4, MeOH

form enantiomers

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20
Q

What is another way to make an alcohol from a ketone/aldehyde with a strong carbon nucleophile?

A

Grignard reagent

21
Q

How do you make a cyanohydrin from an aldehyde/ketone?

A

KCN, HCN

22
Q

In the presence of water, what is a ketone/aldehyde in equilibrium with?

A

Its hydrate

23
Q

How do you synthesize an acetal?

A

An aldehyde/ketone, 2 moles of ROH, acid catalyzed.

24
Q

What is an Acetal?

A

Tetrahedral carbon with two OR groups on it

25
Q

What are two acid catalysts used for acetal formation?

A

TsOH or Sulfuric Acid

26
Q

Are acetals favored at equilibrium for most aldehydes?

A

Yes

27
Q

Are acetals favored at equilibrium for most ketones?

A

No

28
Q

In acetal formation, under acidic conditions, what charge should the reaction species have?

A

A neutral or +1 formal charge

29
Q

In acetal formation, what is synthesized when a Diol is used

A

A cyclic acetal

30
Q

How can you control the reversibility of acetal formation

A

Add/Take away water

remove water: favor acetal
Add water: favor ketone/aldehyde

31
Q

What do you synthesize when an acetal undergoes hydrolysis?

A

An aldehyde/ketone

32
Q

Will an acetal react under base conditions?

A

No
No reaction occurs

33
Q

What is a hemiacetal?

A

The intermediate formed in the conversion of a ketone/aldehyde to an acetal. These are hard to isolate, but cyclic hemiacetals can be isolated

34
Q

When is a cyclic hemiacetal possible?

A

When a compound contains both a carbonyl and a hydroxy group

35
Q

What is created when an aldehyde/ketone is reacted with two moles of thiol
(RSH)?

A

A thioacetal
Works the same way as alcohols, even the cyclic ones

36
Q

How can a thioacetal be converted to an alkane?

A

Raney nickel (RaNi)

37
Q

What is synthesized when an aldehyde/ketone reacts with a primary amine under acidic conditions?

A

an Imine
C=N

38
Q

What does the pH have to be for the formation of an imine?

A

~4-5

Too low: all amines are pronated
Too high: not enough acid to catalyze reaction

39
Q

What is the product?

A

Cyclohexanone imine + water

40
Q

What is the product?

A
41
Q

What is the product?

A
42
Q

What is synthesized when an aldehyde/ketone reacts with a secondary amine under acidic conditions?

A

An enamine

43
Q

What happens when an imine/enamine is reacted with water?

A

It undergoes hydrolysis and reverts back into an aldehyde/ketone

44
Q

Describe the steps of the Wolff-Kishner Reduction

A

It converts a ketone to an alkane

Form hydrazone, then heat with strong base like KOH or potassium tert-butoxide.

  • Use a high-boiling solvent: ethylene glycol, diethylene glycol, or DMSO.
  • A molecule of nitrogen is lost in the last steps of the reaction
45
Q

What do you get when you react an aldehyde/ketone with a phosphorus ylide (RCPPh3)?

A

An alkene (Wittig reaction)

46
Q

How does one synthesize a Wittig reagent?

A

Start with an alkyl halide

1.PPh3
2. BuLi (CH3CH2CH2CH2 Li)

47
Q

What type of alkene is favored when the Wittig reagent is derived from a simple alkyl halide?

A

Z alkene (same side)

48
Q

What type of alkene is favored when the Wittig reagent contains an electron withdrawing group or a sterically bulky group?

A

E alkene (different sides)

Organic Chemistry 2 (14 decks)

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