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MCAT > Chem II: 11-12 > Flashcards

Chem II: 11-12 Flashcards

1
Q

carboxylic acid nomenclature

A

-oic acid

when carboxylic acid is highest priority, carbonyl carbon becomes C1

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2
Q

cyclic carboxylic acid

nomenclature

A

-carboxylic acid

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3
Q

salts of carboxylic acid

nomenclature

A

names beginning with the cation, followed by the name of the acid with the ending -oate

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4
Q

dicarboxylic acid

A

have carboxylic acid group on each end of the molecule

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5
Q

name of dicarboxylic acid with 2 carbons

A

smallest

oxalic acid

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6
Q

name of dicarboxylic acid with 3 carbons

A

malonic acid

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7
Q

dicarboxylic acid

nomenclature

A

-dioic acid

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8
Q

carboxylic acid physical properties

A

similar to those of aldehydes and ketones bc of carbonyl groups

additional hydroxyl group -> hydrogen bonding, another acidic hydrogen

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9
Q

dimers

A

pairs of molecules connected by 2 hydrogen bonds

carboxylic acids can form dimers

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10
Q

how acidic are carboxylic acids in comparison to acids like HCl

A

HCl and other strong acids are much stronger than carboxylic acids

carboxylic acids are just strong for organic compounds

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11
Q

how acidic are dicarboxylic acids in comparison to carboxylic acids?

A

since -COOH groups in carboxylic acids are EQGs, dicarboxylic acids are more acidic because they have two of these groups

but because of the carboxylate anion when one proton is removed, the second proton is less acidic (harder to remove) than the proton of carboxylic acid

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12
Q

beta-dicarboxylic acids

A
  • dicarboxylic acids in which each carboxylic acid is positioned on the beta carbon of the other
  • two carboxylic acids separated by single carbon
  • high acidity of alpha hydrogens
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13
Q

what causes the relatively high acidity of carboxylic acids?

A
  • electron withdrawing oxygen atoms in functional group
  • high stability of carboxylate anion -> resonance stabilized by delocalization with 2 electronegative oxygen atoms
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14
Q

between a monocarboxylic acid, a dicarboxylic acid, and a dicarboxylic acid that has been deprotonated once, which will be most acidic? why?

A

dicarboxylic acid would be most acidic

then monocarboxylic acid

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15
Q

what effects do additional substituents have on the acidity of carboxylic acids?

A
  • electron withdrawing groups make anion more stable -> inc acidity
  • electron donating groups destabilize anion -> dec acidity
  • the close the group is to the carboxylic acid on the molecule, the stronger the effect will be
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16
Q

ester structure

A
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17
Q

ester

nomenclature

A

-oate

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18
Q

amide structure

A
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19
Q

amine structure

A
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20
Q

anhydride structure

A
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21
Q

synthesis of carboxylic acids

A

oxidation of aldehydes and primary alcohols

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22
Q

carboxylic acids cannot be synthesized from…

A

secondary and tertiary alcohols

bc they already have at least 2 bonds to other carbons

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23
Q

synthesis of carboxylic acids

reagents

A
  • dichromate salt (Na2Cr2O7, K2Cr2O7)
  • chromium triozide (CrO3)
  • potassium permanganate (KMnO4)
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24
Q

nucleophilic acyl substitution

mechanism

A
  1. nucleophilic attack/addition
  2. tetrahedral intermediate
  3. carbonyl reforms by kicking off leaving group

favored in either acidic or basic conditions

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25
Q

acyl derivative

A

all molecules with a carboxylic acid derived carbonyl

includes carboxylic acids, amides, esters, anhydrides, others

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26
Q

amide synthesis through nucleophilic acyl substitution

A

carboxylic acid –> amide

nucleophile: ammonia (NH3) or amine

can be carried out in acid or base

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27
Q

lactam

A

amides that are cyclic

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28
Q

esterification

A

condensation reaction with water as a side product

occurs most rapidly with primary alcohols

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29
Q

esterification

mechanism

A

in acidic solution, carbonyl carbon protonated -> enhances polarity of bond -> carbonyl carbon susceptible to nucleophilic attack

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30
Q

lactone

A

esters that are cyclic

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31
Q

lactone

nomenclature

A

-lactone

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32
Q

reduction of carboxylic acids produces… with….

A

primary alcohols

LiAlH4

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33
Q

reduction of carboxylic acids with LiAlH4

mechanism

A

nucleophilic addition of hydride to carbonyl group

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34
Q

decarboxylation

A

complete loss of carboxyl group as carbon dioxide

  • good way of getting rid of a carbon from parent chain
  • 1,3-dicarboxylic acids and other beta keto acids may spontaneously decarboxylate when heated
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35
Q

decarboxylation

mechanism

A

complete loss of carboxyl group as carbon dioxide

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36
Q

saponification

A

long chain carboxylic acids react with sodium or potassium hydroxide -> salt (soap) is formed

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37
Q

micelle

A
  • soap arranges itself in sphericle structures
  • polar heads face outward, where they can be solvated by water
  • nonpolar hydrocarbon chains oriented towards inside
  • nonpolar molecules dissolve in hydrocarbon interior of spherical micelle
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38
Q

what is the result when butanoic acid is reacted with sodium borohydride?

A

not strong enough to reduc carboxylic acids

no reaction

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39
Q

what is the result when butanoic acid is reacted with lithium aluminum hydride?

A

reduce carboxylic to primary alcohol

1-butanol

40
Q

A decarboxylation reaction can occur when there is a(n) ___________________ functional group that is ____ to a Carboxylic Acid functional group.

(A) Carbonyl, α
(B) Carbonyl, β
(C) Alcohol, α
(D) Alcohol, β

A

(B) Carbonyl, β

A decarboxylation reaction can occur when their is a Carbonyl functional group that is β to a Carboxylic Acid functional group.

41
Q

condensation reaction

A

reaction that combines two molecules into one, while losing a small molecule

42
Q

draw 2-octenoic acid

43
Q

What is the common name for Ethanedioic Acid? Draw this structure.

A

Oxalic Acid

44
Q

To form an Anhydride from acetic acid, which of the following will you need for your reaction conditions?

(A) Acid
(B) Base
(C) Polar Aprotic Solvent
(D) Heat

A

(D) Heat
The heat will assist in the condensation. Acetic acid can react with itself by adding just heat.

45
Q

What functional group results when Ammonia is added to a solution containing a Carboxylic Acid?

(A) Carboxylic Acid
(B) Ester
(C) Amide
(D) Carboxylate

A

(D) Carboxylate

Ammonia will act as a base and steal the proton from the Carboxylic Acid. You might be able to force it into becoming an amide using heat, but this may not work.

46
Q

True or false? A long chain carboxylic acid is functionally the same as a fatty acid.

A

True. A long chain carboxylic acid is functionally the same as a fatty acid.

51
Q

what kind of amines can be used for amide synthesis through nucleophilic acyl substitution?

A

only primary and secondary amines because loss of hydrogen is needed

52
Q

lactam nomenclature

A

-lactam

names according to carbon atom bonded to the nitrogen

53
Q

do amides participate in hydrogen bonding?

A

amides may or may not participate in hydrogen bonding depending on the number of alkyl groups they have bonded

54
Q

ester synthesis

A

condensation reaction of carboxylic acids or anhydrides with alcohols

fescher esterification

55
Q

fischer esterification

A

under acidic conditions

carboxylic acid or anhydride + alcohol -> ester

56
Q

fischer esterification

mechanism

57
Q

do esters participate in hydrogen bonding

A

no

lower BPs

58
Q

triaglycerols

A

storage form of fats in the body

esters of long chain carboxylic acids (fatty acids) and glycerol

59
Q

anhydride synthesis

A

condensation of 2 carboxylic acids via nucleophilic acyl substitution

can be formed with just heat

60
Q

anhydride synthesis

mechanism

A

hydroxyl group of one -COOH acts as nucleophile, attacking the carbonyl on the other -COOH

61
Q

anhydride BP compared to related carboxylic acids

A

higher BPs bc of greater weight

62
Q

anhydride nomenclature

symmetrical

asymmetrical

A

symmetrical: substitute word anhydride for acid
asymmetrical: name the two chains alphabetically + anhydride

63
Q

phthalic and sucinic anhydrides

A

cyclic anhydrides arising from intramolecular condensation or dehydration of diacids

65
Q

most to least reactive of functional groups with carbonyls

A

anhydrides (resonance stabilization and EWGs) , esters (EWGs), amides (EDGs)

66
Q

induction

A

distribution of charge across sigma bonds

electrpms are attracted to atos that are more electronegative, generating a dipole

67
Q

conjugation

A

presence of alternating single and multiple bonds

delocalized pi electrons through resonance

68
Q

enones

A

alpha,beta unsaturated carbonyls

69
Q

conjugation and resonance have a ____ effect than induction

70
Q

reactivity of lactams abd lactones

A

certain lactams and lactones are more reactive hydrolysis because they contain more strain

71
Q

beta lactams

A
  • four membered cyclic amides
  • highly reactive due to significant ing strain (torsional and angle strain)
  • part of core structure for antibiotic families
72
Q

rank the following molecules by decreasing reactivity to OR-: acetamide, acetic anhydride, ethyl acetate

A

acetic anhydride, ethyl acetate, acetamide

73
Q

what is responsible for the increased rate of hydrolysis in beta lactams?

A

beta-lactams are susceptible to hydrolysis due to the high level of ring strain, which is due to both torsional strain (eclipsing interactions) and angle strain (deviation from 109.5°).

74
Q

what properties account for the differences in reactivity seen between anhydrides, esters, and amides with nucleophiles?

A

Electronic effects like induction have some effect on the reactivity of the carbonyl in these three functional groups. Differences in resonance also explain the increased reactivity of anhydrides, in particular. Steric effects could also be significant, depending on the specific leaving group present.

75
Q

anhydride nucleophilic acyl substitution with ammonia

mechanism

A

produces amide and carboxylic acid

nucl: ammonia
electrophile: carbonyl carbon

LG: carboxylic acid

76
Q

anhydride nucleophilic acyl substitution with alcohol

mechanism

A

produces ester and carboxylic acid

nucl: alcohol
electrophile: carbonyl carbon

LG: carboxylic acid

77
Q

converting anhydrides back to carboxylic acid

mechanism

A

expose them to water

anhydride should be symmetric

78
Q

transesterification

A

alcohols act as nucl and displace esterifying group on ester

79
Q

hydrolysis of amides

acidic vs basic condtns

A
  • highly acidic conditions
    • carbonyl oxygen becomes protonated -> nucl attack
    • product: carboxylic acid
  • highly basic conditions
    • nucl is hydroxide ion
    • product: carboxylate anion
80
Q

hydrolysis of amide

acidic conditions

mechanism

A

produce carboxylic acid

81
Q

in the formation of an amide from ammonia and an anhydride, what serves as the nucleophile? the electrophile?

A

nucl: ammonia
electrophile: one of the carbonyl carbons of the anhydride

82
Q

Draw Diethyl Malonate.

83
Q

Draw Methyl Cyclohexanecarboxylate

84
Q

Draw Ethanamide (Acetamide)

85
Q

Draw N-methyl Propanamide

86
Q

Draw N,4-dimethyl Benzamide

87
Q

Why does resonance dominate induction in the case of an amide?

A

This is because nitrogen is not very electronegative, so it holds onto its electrons less tightly and will more readily donate them to form the resonance structure.

88
Q

Under which of the following conditions will a Fischer Esterification occur?

I. Acidic conditions with carboxylic acids and alcohols
II. Basic conditions with lactones and alcohols
III. Acidic conditions with anhydrides and alcohols

(A) I only
(B) I and III only
(C) II and III only
(D) I, II and III

A

(B) I and III only

A Fischer Esterification can occur in either of the following conditions:

I. Acidic conditions with carboxylic acids and alcohols
II. Acidic conditions with anhydrides and alcohols

MCAT (26 decks)

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