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MCAT > Organic Reactions > Flashcards

Organic Reactions Flashcards

1
Q

What does an acid-base reaction form?

A

Conjugate acid and conjugate base

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2
Q

What is required of the reactants for an acid-base reaction to run?

A

Reactants are stronger than the products

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3
Q

What is the definition of a lewis acid?

A

Electron acceptor, electrophile

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4
Q

Is a lewis acid an electrophile or nucleophile?

A

Electrophile

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5
Q

Is a lewis base an electrophile or nucleophile?

A

Nucleophile

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6
Q

What is the definition of a lewis base?

A

Electron donor, nucleophile

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7
Q

Is an electron donor a lewis acid or base?

A

Base

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8
Q

Is an electron acceptor a lewis acid or base?

A

Acid

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9
Q

What is a coordinate covalent bond?

A

Bond in which both bonding e- come from the same atom

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10
Q

What is the definition of a Bronsted-Lowry acid?

A

H+ donor

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11
Q

What is the definition of a Bronsted-Lowry base?

A

H+ acceptor

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12
Q

Is a proton acceptor a Bronsted-Lowry acid or base?

A

Base

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13
Q

Is a proton donor a Bronsted-Lowry acid or base?

A

Acid

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14
Q

What is the definition of an amphoteric molecule?

A

Can act as a Bronsted-Lowry acid or base depending on the solution

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15
Q

Is water an acid or base in a basic solution and what product is formed?

A

Acid, donates H+ to make OH-

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16
Q

Is water an acid or base in an acidic solution and what product is formed?

A

Base, accepts H+ to make H3O+

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17
Q

What are some examples of amphoteric molecules?

A

H2O
AL(OH)3
HCO3-
HSO4-

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18
Q

What is Ka and how is it calculated?

A

Acid Dissociation Constant, represents the strength of an acid

Ka=([H+][A-])/[HA]

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19
Q

pKa

A

-log(Ka)

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20
Q

Does a smaller Ka indicate a stronger or weaker acid?

A

Stronger

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21
Q

What pKa defines a strong acid?

A

Lower,

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22
Q

What does it mean if an acid is strong?

A

Dissociates in aqueous solution

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23
Q

Does acidity increase or decrease as you go down the periodic table?

A

Increase

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24
Q

Does acidity increase or decrease as you go up the periodic table?

A

Decrease

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25
Q

Does acidity increase or decrease with electronegativity?

A

Increase

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26
Q

Which hydrogen is easily lost in a carbonyl compound?

A

Alpha hydrogen (bonded to the alpha carbon, which is next to the carbonyl group)

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27
Q

Is electro and nucleophilicity a thermodynamic or kinetic property?

A

Kinetic property based on reaction rates

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28
Q

What is a kinetic property based on?

A

Reaction rates

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29
Q

What is a thermodynamic property based on?

A

Reaction equilibrium

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30
Q

Is acid-base strength a thermodynamic or kinetic property?

A

Thermodynamic based on acid-base equilibrium

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31
Q

What are nucleophiles?

A

“nucleus loving” with lone pairs or pi bonds that can form new bonds

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32
Q

Is nucleophilicity similar to acidity or basicity?

A

Basicity

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33
Q

Are nucelophiles usually positive or negative?

A

Negative

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34
Q

Do electronegative atoms increase or decrease nucleophilicity?

A

Decrease because they are electron withdrawing (reduce negative charge)

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35
Q

Do bulky groups increase or decrease nucleophilicity?

A

Decrease because they provide steric hindrance

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36
Q 
Rank the following in decreasing reactivity:
Ester
Amide
Anhydride
Carboxylic Acid
A

Anhydride>Carboxylic Acid/ Ester > Amide

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37
Q

Do protic solvents increase or decrease nucleophilicity?

A

Decrease by protonating the nucleophile

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38
Q

What are electrophiles?

A

“Electron-loving” species with a positive charge or positively polarized atom that acts as an electron acceptor

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39
Q

Do electrophiles behave like acids or bases?

A

Acids

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40
Q

Heterolytic Reactions

A

When a bond is broken and both electrons go to the same atom

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41
Q

Are weak bases good or bad leaving groups?

A

Good

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42
Q

Why are weak bases good leaving groups?

A

They are stable with extra electrons

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43
Q

How many steps is an Sn1 reaction?

A

Two

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44
Q

What are the step(s) of an Sn1 reaction?

A
  1. Leaving group leaves and generates a carbocation

2. Nucleophile attacks the carbocation

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45
Q

What is the stereochemistry of the products of an Sn1 reaction?

A

Usually racemic

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46
Q

What reaction order is an Sn1 reaction?

A

First order

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47
Q

Which step is rate-limiting in an Sn1 reaction?

A

First step

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48
Q

What type of compounds are best suited for Sn1 reactions?

A

Bulky, more substituted alkanes

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49
Q

How many steps is an Sn2 reaction?

A

One

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50
Q

What are the step(s) of an Sn2 reaction?

A
  1. Back-side attack by nucleophile at the same time the leaving group leaves
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51
Q

What is the stereochemistry of the products of an Sn2 reaction?

A

Inverted compared to the original

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52
Q

What reaction order is an Sn2 reaction?

A

Second order

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53
Q

What type of compounds are best suited for an Sn2 reaction?

A

Strong nucleophiles and alkanes without steric hindrance

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54
Q

What happens in redox reactions?

A

The oxidation states of the reactants change

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55
Q

What type of compounds are best suited for an Sn2 reaction?

A

Strong nucleophiles and alkanes without steric hindrance

56
Q

What is the most oxidized form of carbon and what is the oxidation state?

57
Q

What is the most reduced form of carbon and what is the oxidation state?

58
Q

Is oxidation loss or gain of electrons?

59
Q

Is reduction loss or gain of electrons?

60
Q

Does an oxidizing agent accept or donate electrons?

61
Q

Is an oxidizing agent oxidized or reduced?

62
Q

Does a reducing agent accept or donate electrons?

63
Q

Is a reducing agent oxidized or reduced?

64
Q

Does reactivity increase or decrease with oxidation?

65
Q

How are carbonyl compounds protected in reaction?

A

Addition of two equivalents diol (or geminal diol) to form acetal or ketal

66
Q

What is an acetal?

A

Carbon bound to two OR groups from alcohol (with other two bonds to R groups and H)

67
Q

What is a ketal?

A

Carbon bound to two OR groups from alcohol (with other two bonds to R groups)

68
Q

What is the difference between acetal and ketal?

A

One bond to H in acetal, all bound to R groups in ketal

69
Q

How are protecting groups removed?

A

Acid and heat

70
Q

How are alcohols protected in reaction?

A

Reduced to t-butyl ethers

71
Q

How is alcohol oxidized to an aldehyde?

72
Q

Is alcohol to aldehyde oxidation or reduction?

73
Q

What is phenol?

A

-OH attached to aromatic ring

74
Q

Is phenol more or less acidic than C-chain alcohols and why?

A

More because of resonance stabilization through the ring

75
Q

What is ortho designation?

A

Two groups on adjacent carbons in ring

76
Q

What is meta designation?

A

Two groups separated by one C in a ring

77
Q

What is para designation?

A

Two groups on the opposite sides of a ring

78
Q

Do alcohols have higher or lower boiling points than their alkane counterparts and why?

A

Higher due to inter molecular hydrogen bonding

79
Q

Rank the following by increasing BP:

Aldehyde
Alkane
Alcohol
Ketone

A

Alkane
Aldehyde/Ketone
Alcohol

80
Q

What happens when a primary alcohol is reacted with PCC?

81
Q

What happens when a primary alcohol is reacted with a strong oxidizing agent?

A

Carboxylic Acid

82
Q

What happens when a secondary alcohol is reacted with PCC?

83
Q

What happens when a secondary alcohol is reacted with a strong oxidizing agent?

84
Q

What is sodium dichromate?

85
Q

What is potassium dichromate?

86
Q

Is Na2Cr2O7 an oxidizing or reducing agent?

87
Q

Is LiAlH4 an oxidizing or reducing agent?

88
Q

What is mesylate?

A

S double bound to two O, single bound to one O with a negative charge, and single bound to methyl group
SO3CH3-

89
Q

What is tosylate?

A

S double bound to two O, single bound to one O with a negative charge, and single bound to benzene with a methyl group in para position

90
Q

What is the purpose of reacting mesylates and tosylates with alcohols?

A
  1. Makes them into better leaving groups

2. Can serve as protecting groups as they will not react with oxidizing agents

91
Q

Do mesylates react with oxidizing agents?

92
Q

Do tosylates react with oxidizing agents?

93
Q

What is a quinone?

A

6 carbon ring with two double bonds opposite one another and two =O in para position

94
Q

How are quinones formed?

A

Oxidation of phenol

95
Q

What is formed when phenol is oxidized?

96
Q

What are two examples of biological quinones?

A

Vitamin K1 and K2

97
Q

What is formed when quinone is oxidized?

A

Hydroxyquinone

98
Q

What is hydroxyquinone?

A

Quinone with hydroxyl group

99
Q

What is butyraldehyde?

100
Q

What is valeraldehyde?

101
Q

What is an aldehyde attached to a ring called?

A

Carbaldehyde

102
Q

What is carbaldehyde?

A

An aldehyde attached to a ring

103
Q

Do carbonyls act as electophiles or nucleophiles?

104
Q

When do carbonyls act as electrophiles?

A

Nucleophile attacks the carbon which is partially positive due to electron-withdrawing properties of Oxygen

105
Q

Are aldehydes or ketones more electrophilic and why?

A

Aldehydes because they lack steric hindrance and do not have electron-donating alkyl groups

106
Q

Are alkyl groups electron donating or withdrawing

107
Q

Do electron donating groups increase or decrease electrophilicity?

108
Q

Do electron withdrawing groups increase or decrease electrophilicity?

109
Q

What does a ketone plus nucleophile form?

A

Secondary alcohol

110
Q

What is a hydration reaction?

A

Formation of geminal diols from ketone/aldehydes with water

111
Q

What happens when water is added to aldehyde?

A

Geminal diol

112
Q

What is a hemiacetal and how is it formed?

A

Addition of one equivalent of alcohol to acetal

C boudn to R, OH, OR, and H

113
Q

What happens when ammonia is added to carbonyl?

A

Formation of imine through loss of water

114
Q

What is the strucute of an imine?

A

C bound to two R groups and double bound to N-H

115
Q

Hydrazine

116
Q

Semicarbide

A

H2N-NH-carbonyl-NH2

117
Q

Hydrogen cyanide

118
Q

What is cyanohydrin?

A

C single bound to two R groups, OH, and -CN

119
Q

How is cyanohydrin formed?

A

HCN plus ketone/aldehyde

120
Q

How are ketones and aldehydes transformed to alcohols?

A

Reduction by hydride reagents

121
Q

What are examples of hydride reagents?

A

LiAlH4

NaBH4

122
Q

What is an alpha hydrogen?

A

Hydrogen attached to alpha carbon (carbon attached to carbonyl carbon)

123
Q

When do carbonyls act as nucelophiles?

A

When ketone/aldehyde is reacted with base, alpha carbon is lost and carbanion is formed

124
Q

What is keto-enol tautomerization?

A

Move H and double bond in ketone - C=C and H transferred to O to make OH

125
Q

Is keto or enol form favored in tautomerization?

126
Q

Enamination

A

Tautomerization between imine and enamine

Move H and double bond in imine - C=C bound to NH2

127
Q

Is imine or enamine form favored in tautomerization?

128
Q

What are the steps of the Michael addition?

A
  1. Base deprotonates the alpha carbon of ketone/aldehyde forming a carbanion
  2. Carbanion attacks a double bond of an alpha-beta unsaturated carbonyl
129
Q

What is a kinetic enolate?

A

Double bond moves to the less substituted alpha carbon

130
Q

Under what reaction conditions is a kinetic enolate formed?

A

Fast
Irreversible
Strong, bulky base
Lower temperature

131
Q

Under what reaction conditions is a thermodynamic enolate formed?

A

Slow
Reversible
Higher temperature
Weak, small base

132
Q

What is a thermodynamic enolate?

A

Double bond moves to the more substituted alpha carbon

133
Q

Is a kinetic or thermodynamic enolate more stable?

A

Thermodynamic

134
Q

What happens to an aldehyde or ketone in the presence of a base?

A

Aldol condensation

135
Q

What is an aldol condensation?

A

Aldehyde or ketone acts as both a nucleo and electrophile to form a C-C bond in the presence of a base

136
Q

What is an aldol?

A

Molecule that contains an alcohol and an aldehyde

MCAT (31 decks)

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