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MCAT OChem > Carbonyls and Amines > Flashcards

Carbonyls and Amines Flashcards

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MCAT flashcards
1
Q

carbonyl

A

carbon double bonded to an oxygen

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2
Q

functional groups that contain carbonyls

A

aldehydes, ketones, carboxylic acids, amides, esters

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3
Q

2 things to think when see carbonyl….

A

planar stereochemistry, partial + charge on C/partial - charge on O

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4
Q

aldehydes and ketones are more ___ and have higher _____ than alkanes and alkenes of similar weight

A

more polar, higher boiling points (lower boiling points than corresponding alcohols - cant H bond with each other)

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5
Q

a carbon that is attached to a carbonyl carbon is in the ____ ____ and is called an ____ ____

A

alpha position, alpha carbon

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6
Q

aldehyde and ketone commonly donate one of their….

A

alpha hydrogens

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7
Q

enolate ion

A

alpha carbon anions, stabilized by resonance

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8
Q

dicarbonyl

A

when beta carbon is also carbonyl, increases acidity of alpha hydrogen between carbonyl, making it more acidic than water or alcochol
enol from becomes more stable due to internal hydrogen bonding and resonance

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9
Q

aldehydes are slightly more ____ than ketones

A

acidic and reactive

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10
Q

keto-enol tautomerization

A

ketones and aldehydes exist at room temp as enol tautomers

proton shift, reaction at equilibrium not a resonance

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11
Q

aldehydes and ketones react with alcohols to form…

A

hemiacetals and hemiketals

hemiacetal –> acetal and hemiketal –> ketal if second molar eqiv. of alcohol added

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12
Q

because acetals and ketals are unreactive toward ____, they are often used as blocking groups

A

bases

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13
Q

when aldehydes and ketones are dissolved in aq. solution they establish an equilibrium with their _____

A

hydrate, a geminal diol

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14
Q

Aldol condensation

A

when one aldehyde reacts with another, when one ketone reacts with another, or when an aldehyde reacts with a ketone
catalyzed by acid or base
1. base takes alpha H leaving enolate ion
2. enoalte ion acts as nucleophile, attacks carbonyl C to from aloxide ion
3. removes proton from water to aldol
4. aldol is unstable, dehydrated by heat/base to become an enal

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15
Q

halogenation of a ketone

A

halogens add to ketones at the alpha carbon in the presence of a base or an acid

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16
Q

haloform reaction

A

when base used with methyl ketone in halogenation of ketone reaction, alpha carbon becomes completely halogenated
trihalo product reacts further with the base —> carobxylic acid and a halofrom (HCX3)

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17
Q

Wittig reaction

A

converts a ketone to an alkene

phosphorus ylid is used

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18
Q

ylid

A

neutral molecule with a negatively charged carbanion

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19
Q

alpha-beta unsaturated carbonyl

A

carbocation at carbonyl carbon is stabilized by resonance

enol-keto tautomers

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20
Q

formic acid/methanoic acid

A

H-C=O(-OH)

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21
Q

acetic acid/ethanoic acid

A

H3C-C=O(-OH)

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22
Q

benzoic acid

A

benzene-C=O(-OH)

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23
Q

carboxylic acids are able to make strong double ____ to form a dimer

A

hydrogen bonds

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24
Q

decarboxylation

A

when a carboxylic acid loses CO2

activation energy high

25
Q

acyl group

A

R-C=O

26
Q

____ ____ are the most reactive of the carboxylic acid derivatives because of the ____

A

acid chlorides [ R-C=O(-Cl) ] because of the stability of the Cl- leaving group
acid chlorides love nucleophiles

27
Q

hydrolysis of carboxylic acid derivatives –>

A

carboxylic acid

28
Q

alcohols react with carboxylic acids through nucleophilic substitution to form ____

A

esters

29
Q

transesterification

A

trading alkoxy groups on an ester

30
Q

acetoacetic ester synthesis

A

production of a ketone from acetoacetic ester due to the strongly acidic properties of the alpha hydrogen

31
Q

amides are formed when an _____ acting as a nucleophile substitutes at the carbonyl of a carboxylic acid or one of its derivatives

A

amine

32
Q

in all of the reactions with carboxylic acid derivatives, the carbonyl carbon is acting as the ____ in _____ ____

A

acting as the substrate in acyl substitution

33
Q

carboxylic acids and their derivatives undergo ____ ____, while aldehydes and ketones prefer ____ ____

A

carboxylic acids: acyl substitution

aldehydes and ketones: nucleophilic addition

34
Q

amines

A

derivatives of ammonia

35
Q

ammonia

A

NH3

36
Q

primary amine

A

RNH2

37
Q

secondary amine

A

R2NH

38
Q

tertiary amine

A

R3N

39
Q

quaternay amine

A

R4N+

40
Q

nitrogen can take ____ bond

A

3 or 4

41
Q

3 considerations for nitrogen containing compounds

A
  • may act as Lewis base donating their lone pair of e-‘s
  • may act as nucleophile where the lone pair of e-s attacks a positive charge
  • nitrogen can take on a fourth bond becoming + charged
42
Q

ammonia and amines act as ___ bases by donating their lone pair of e-s

A

weak bases

43
Q

general trend of amine basicity from highest to lowest when the functional groups are e- donating

A

secondary, primary, ammonia, aromatic amines

44
Q

ammonia and amines ___ ___ which raises boiling point and increase solubility

A

hydrogen bond

45
Q

amines react with aldehydes and ketones losing water to produce ___ and ___

A

imines and enamines

46
Q

Wolff-Kishner Reduction

A

reduce a ketone or aldehyde by removing the oxygen and replacing it with two hydrogens
(can do same by adding hot acid, but some cant survive it)

47
Q

amine alkylation

A

NH3 + RX –> RNH2 + HX

nucleophilic substitution, amine acting as nucleophile

48
Q

Hofmann elimination

A

heating the quarternary ammonium hydroxide, to form an alkene
least stable alkene is major product

49
Q

primary amines react with nitrous acid to form____

A

diazonium salts, only aromatic amines work

50
Q

acetamide

A

H3C-C=O(-NH2)

51
Q

N-ethylacetamide

A

H3C-C=O(-NHC2H5)

52
Q

amides can behave as…

A

weak acids or weak bases

53
Q

amides are ____ than amine due to the e- withdrawing properties of the carbonyl

A

less basic than amines

54
Q

cyclic amides are called

A

lactams

55
Q

beta-lactams

A

4 membered rings, cyclic amides, highly reactive due to ring strain

56
Q

Hofmann degradation

A

primary amides react with strongly basic solutions of chlorine or bromine to form primary amines with carbon dioxide as byproduct
-can produce amines with primary, secondary, or tertiary alkyl position (other methods rely on SN2 and prevent production of amines on tertiary carbons)

57
Q

phosphoric acid

A

P(OH)3=O

58
Q

when heated phosphoric acid forms_____

A

phosphoric anhydrides

MCAT OChem (4 decks)

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