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CHM2911 > Organic Chemistry I > Flashcards

Organic Chemistry I Flashcards

1
Q

Define

Anti-periplanar

A

describes two bonds that are antiparallel in the plane they define (i.e. C-H and C-LG bonds)

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2
Q

Define

Backside attack

A

The SN2 mechanism in which the nucleophile attacks the α-carbon from a direction directly opposite to the C-LG bond. Results in inversion of stereochemical configuration

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3
Q

Define

Bromination

A

Any reaction or process in which bromine (and no other elements) are introduced into a molecule

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4
Q

Define

Carboanion

A

an organic anion in which the negative charge is located on a carbon atom

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5
Q

Define

Carbocation

A

A carbon that carries a positive charge. They are highly unstable and are prone to rearrangement. SN1 and E1 reactions proceed through this common intermediate

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6
Q

Define

Chirality

A

The geometric property of a rigid object (or spatial arrangement of points or atoms) of being non-superposable on its mirror image

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7
Q

Define

Concerted

A

A single step mechanism. Describes SN2 and E2 mechanisms

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8
Q

Define

E1 reaction

A

A reaction where a β-hydrogen is Eliminated to form a double bond. They go through a carbocation intermediate. Somewhat similar to the E2 reaction

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9
Q

Define

E2 reaction

A

reaction in which a β-hydrogen and a leaving group are removed to form a double bond. The reaction is so named because it is bimolecular (2 molecules) and because it involves the Elimination of a β-hydrogen

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10
Q

Define

Electron delocalisation

A

electrons in a molecule, ion or solid metal that are not associated with a single atom or a covalent bond

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11
Q

Define

Electrophile

A

an electron pair acceptor. They are positively charged or neutral species having vacant orbitals that are attracted to an electron rich centre. It participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile

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12
Q

Define

Electrophilic addition

A

a reaction between an electrophile and nucleophile, adding to double or triple bonds

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13
Q

Define

Elimination reaction

A

a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism

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14
Q

Define

Finkelstein reaction

A

an SN2reaction (Substitution Nucleophilic Bimolecular reaction) that involves the exchange of one halogen atom for another

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15
Q

Define

First-order reaction

A

a chemical reaction in which the rate of reaction is directly proportional to the concentration of the reacting substance

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16
Q

Define

Frontside attack

A

A disproved SN2 mechanism in which the nucleophile attacks the α-carbon from the same side as the C-LG bond. If this mechanism was valid, it would result in retention of stereochemical configuration

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17
Q

Define

Hybridisation

A

the concept of mixing atomic orbitals into new hybrid orbitals (with different energies, shapes, etc., than the component atomic orbitals) suitable for the pairing of electrons to form chemical bonds in valence bond theory

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18
Q

Define

Hydroboration

A

the addition of a hydrogen-boron bond to C-C, C-N, and C-O double bonds, as well as C-C triple bonds

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19
Q

Define

Hyperconjugation

A

the stabilising interaction that results from the interaction of the electrons in a σ-bond (usually C-H or C-C) with an adjacent empty or partially filled p-orbital or a π-orbital to give an extended molecular orbital that increases the stability of the system

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20
Q

Define

Lewis structure

A

a diagram that shows the covalent bonds and lone electron pairs in a molecule

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21
Q

Define

Markivnikov’s rule

A

In an addition reaction of a protic acid HX (hydrogen chloride, hydrogen bromide, or hydrogen iodide) to an alkene or alkyne, the hydrogen atom of HX becomes bonded to the carbon atom that had the greatest number of hydrogen atoms in the starting alkene or alkyne

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22
Q

Define

Mecuriation

A

Any reaction that introduces a covalent mercury bond into a compound

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23
Q

Define

Nucleophile

A

a chemical species that donates an electron pair to form a chemical bond in relation to a reaction. All molecules or ions with a free pair of electrons or at least one pi bond can act as one. Because they donate electrons, they are by definition Lewis bases

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24
Q

Define

Nucleophilic substitution reactions

A

a fundamental class of reactions in which an electron rich nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms to replace a leaving group

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25
Q

Define

Oxymecuration

A

an electrophilic addition organic reaction that transforms an alkene into a neutral alcohol

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26
Q

Define

Radical

A

an atom, molecule, or ion that has an unpaired valence electron

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27
Q

Define

Reactive intermediates

A

a molecular entity that is formed from the reactants (or preceding intermediates) and reacts further to give the directly observed products of a chemical reaction

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28
Q

Define

Rearrangment reactions

A

a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule

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29
Q

Define

Regioselectivity

A

the preference of one direction of chemical bond making or breaking over all other possible directions

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30
Q

Define

Second-order reaction

A

a type of chemical reaction that depends on the concentrations of one-second order reactant or two first-order reactants. This reaction proceeds at a rate proportional to the square of the concentration of one reactant or the product of the concentrations of two reactants

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31
Q

Define

SN1 reaction

A

A reaction in which a Nucleophile Substitutes for a leaving group. It goes through a carbocation intermediate

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32
Q

Define

SN2 reaction

A

reaction is a bimolecular (2 molecules) reaction involving the Substitution of a Nucleophile for a leaving group

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33
Q

Define

Sp hybridisation

A

a type of hybridization where the s orbital overlaps with only one p orbital

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34
Q

Define

Sp2 hybridisation

A

The process of intermixing of one S and two P orbitals to give three identical hybrid orbitals

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35
Q

Define

Sp3 hybridisation

A

refers to the mixing of one s and three p orbitals to form four sp3 hybridized orbitals

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36
Q

Define

Stereogenic centre

A

any location in a molecule where the interchange of any two groups gives a new stereoisomer

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37
Q

Define

Stereoselectivity

A

the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non-stereospecific creation of a new stereocenter or during a non-stereospecific transformation of a pre-existing one

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38
Q

Define

Steric effects

A

an influence on a reaction’s course or rate determined by the fact that all of the atoms within a molecule occupy space, thus certain collision paths are either disfavored or favored

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39
Q

Define

Zaitsev rule

A

an empirical rule for predicting the favored alkene product(s) in elimination reactions

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40
Q

Definition

describes two bonds that are antiparallel in the plane they define (i.e. C-H and C-LG bonds)

A

Anti-periplanar

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41
Q

Definition

The SN2 mechanism in which the nucleophile attacks the α-carbon from a direction directly opposite to the C-LG bond. Results in inversion of stereochemical configuration

A

Backside attack

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42
Q

Definition

Any reaction or process in which bromine (and no other elements) are introduced into a molecule

A

Bromination

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43
Q

Definition

an organic anion in which the negative charge is located on a carbon atom

A

Carboanion

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44
Q

Definition

A carbon that carries a positive charge. They are highly unstable and are prone to rearrangement. SN1 and E1 reactions proceed through this common intermediate

A

Carbocation

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45
Q

Definition

The geometric property of a rigid object (or spatial arrangement of points or atoms) of being non-superposable on its mirror image

A

Chirality

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46
Q

Definition

A single step mechanism. Describes SN2 and E2 mechanisms

A

Concerted

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47
Q

Definition

A reaction where a β-hydrogen is Eliminated to form a double bond. They go through a carbocation intermediate. Somewhat similar to the E2 reaction

A

E1 reaction

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48
Q

Definition

reaction in which a β-hydrogen and a leaving group are removed to form a double bond. The reaction is so named because it is bimolecular (2 molecules) and because it involves the Elimination of a β-hydrogen

A

E2 reaction

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49
Q

Definition

electrons in a molecule, ion or solid metal that are not associated with a single atom or a covalent bond

A

Electron delocalisation

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50
Q

Definition

an electron pair acceptor. They are positively charged or neutral species having vacant orbitals that are attracted to an electron rich centre. It participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile

A

Electrophile

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51
Q

Definition

a reaction between an electrophile and nucleophile, adding to double or triple bonds

A

Electrophilic addition

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52
Q

Definition

a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism

A

Elimination reaction

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53
Q

Definition

an SN2reaction (Substitution Nucleophilic Bimolecular reaction) that involves the exchange of one halogen atom for another

A

Finkelstein reaction

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54
Q

Definition

a chemical reaction in which the rate of reaction is directly proportional to the concentration of the reacting substance

A

First-order reaction

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55
Q

Definition

A disproved SN2 mechanism in which the nucleophile attacks the α-carbon from the same side as the C-LG bond. If this mechanism was valid, it would result in retention of stereochemical configuration

A

Frontside attack

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56
Q

Definition

the concept of mixing atomic orbitals into new hybrid orbitals (with different energies, shapes, etc., than the component atomic orbitals) suitable for the pairing of electrons to form chemical bonds in valence bond theory

A

Hybridisation

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57
Q

Definition

the addition of a hydrogen-boron bond to C-C, C-N, and C-O double bonds, as well as C-C triple bonds

A

Hydroboration

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58
Q

Definition

the stabilising interaction that results from the interaction of the electrons in a σ-bond (usually C-H or C-C) with an adjacent empty or partially filled p-orbital or a π-orbital to give an extended molecular orbital that increases the stability of the system

A

Hyperconjugation

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59
Q

Definition

a diagram that shows the covalent bonds and lone electron pairs in a molecule

A

Lewis structure

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60
Q

Definition

In an addition reaction of a protic acid HX (hydrogen chloride, hydrogen bromide, or hydrogen iodide) to an alkene or alkyne, the hydrogen atom of HX becomes bonded to the carbon atom that had the greatest number of hydrogen atoms in the starting alkene or alkyne

A

Markivnikov’s rule

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61
Q

Definition

Any reaction that introduces a covalent mercury bond into a compound

A

Mecuriation

62
Q

Definition

a chemical species that donates an electron pair to form a chemical bond in relation to a reaction. All molecules or ions with a free pair of electrons or at least one pi bond can act as one. Because they donate electrons, they are by definition Lewis bases

A

Nucleophile

63
Q

Definition

a fundamental class of reactions in which an electron rich nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms to replace a leaving group

A

Nucleophilic substitution reactions

64
Q

Definition

an electrophilic addition organic reaction that transforms an alkene into a neutral alcohol

A

Oxymecuration

65
Q

Definition

an atom, molecule, or ion that has an unpaired valence electron

A

Radical

66
Q

Definition

a molecular entity that is formed from the reactants (or preceding intermediates) and reacts further to give the directly observed products of a chemical reaction

A

Reactive intermediates

67
Q

Definition

a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule

A

Rearrangment reactions

68
Q

Definition

the preference of one direction of chemical bond making or breaking over all other possible directions

A

Regioselectivity

69
Q

Definition

a type of chemical reaction that depends on the concentrations of one-second order reactant or two first-order reactants. This reaction proceeds at a rate proportional to the square of the concentration of one reactant or the product of the concentrations of two reactants

A

Second-order reaction

70
Q

Definition

A reaction in which a Nucleophile Substitutes for a leaving group. It goes through a carbocation intermediate

A

SN1 reaction

71
Q

Definition

reaction is a bimolecular (2 molecules) reaction involving the Substitution of a Nucleophile for a leaving group

A

SN2 reaction

72
Q

Definition

a type of hybridization where the s orbital overlaps with only one p orbital

A

Sp hybridisation

73
Q

Definition

The process of intermixing of one S and two P orbitals to give three identical hybrid orbitals

A

Sp2 hybridisation

74
Q

Definition

refers to the mixing of one s and three p orbitals to form four sp3 hybridized orbitals

A

Sp3 hybridisation

75
Q

Definition

any location in a molecule where the interchange of any two groups gives a new stereoisomer

A

Stereogenic centre

76
Q

Definition

the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non-stereospecific creation of a new stereocenter or during a non-stereospecific transformation of a pre-existing one

A

Stereoselectivity

77
Q

Definition

an influence on a reaction’s course or rate determined by the fact that all of the atoms within a molecule occupy space, thus certain collision paths are either disfavored or favored

A

Steric effects

78
Q

Definition

an empirical rule for predicting the favored alkene product(s) in elimination reactions

A

Zaitsev rule

79
Q
A
80
Q
A
81
Q
A
82
Q
A
83
Q

What are the three different types of hybridisation that can occur?

A
84
Q

How many σ-bonds does sp3 hydridisation have?

A

4 σ-bonds

s1p3: 1+3=4

85
Q

What is the bond angle of an sp2 carbon?

A

120 degrees

86
Q

In ethene, each C atom has __ sp2 orbital(s) and __ p orbital(s)

A

In ethene, each C atom has 3 sp2 orbitals and 1 p orbital

87
Q

What is the bond angle of a sp carbon?

A

180 degrees

88
Q
A
89
Q
A
90
Q
A
91
Q

What are the two electron deficient states that a carbon molecule can exist in?

A

Radical and carbocation

92
Q

True or False:

Carbocations are electrophilic

A

True

They are electron deficient and therefore seek out more electrons

93
Q

True or False:

Carboanions are electrophilic

A

False

They are nucleophilic since they are electron rich

94
Q

Carbocations have __ s and __ p orbitals

A

Carbocations have 1 s and 2 p orbitals

95
Q

What hybridisation state are carbocations in?

A

sp2

96
Q

What hybridisation state are carbon centered radicals in?

A

sp2

97
Q

What hybridisation state are carboanions in?

A

sp3

98
Q
A
99
Q

When drawing resonance contributors, how can electrons be moved?

A
  1. Move π electrons toward a positive charge or toward a π bond
  2. Move lone-pair electrons toward π bond
  3. Move a single non-bonding electron (or charge) toward a π bond
100
Q
A
101
Q
A
102
Q
A
103
Q

List the carbocations in order of increasing stability

Why is this the case?

A

3° > 2° > 1° > methyl

This is because the charge can be delocalised over a greater number of nuclei

104
Q
A
105
Q

____________ donate high-energy electrons to electrophiles

__________ have a low-energy vacant orbital

A

Nucleophiles donate high-energy electrons to electrophiles

Electrophiles have a low-energy vacant orbital

106
Q

__________are negatively charged or neutral species with a pair of electrons

____________are neutral or positively charged species with an empty atomic orbital

A

Nucleophiles are negatively charged or neutral species with a pair of electrons

Electrophiles are neutral or positively charged species with an empty atomic orbital

107
Q
A
108
Q
A
109
Q

What happens in a general nucleophilic substitution reaction?

A

A nucleophile attacks a sp3 hybridised carbon and the leaving group leaves

110
Q

If a stable carbocation can’t form then a SN1/SN2 (choose one) reaction mechanism is not possible

A

If a stable carbocation can’t form then a SN1 reaction mechanism is not possible

111
Q

What reaction mechanism is this?

A

SN1 mechanism

112
Q

What reaction mechanism is this?

A

SN2 mechanism

113
Q

An SN2 reaction is concerted and hence any 3D stereochemical information is _________ and the stereochemistry of the stereogenic centre that is attacked by the nucleophile is ________

A

An SN2 reaction is concerted and hence any 3D stereochemical information is maintained and the stereochemistry of the stereogenic centre that is attacked by the nucleophile is inverted

114
Q
A
115
Q

What determines the rate of an SN1 reaction?

A

The concentration of the alkyl halide

(if the concentration of the alkyl halide doubles, the rate doubles)

116
Q

What determines the rate of an SN2 reaction?

A

The rate depends on the concentration of both reagents

(if the concentration of the alkyl halide or the nucleophile doubles, the rate doubles)

117
Q
A
118
Q
A
119
Q
A
120
Q
A
121
Q
A
122
Q

What type of solvent favours an SN2 reaction?

A

A polar, aprotic solvent like DMF or DMSO

123
Q

What type of solvent favours an SN1 reaction?

A

A polar, protic solvent like H2O, R-OH, R-COOH

124
Q
A
125
Q
A
126
Q
A
127
Q
A
128
Q
A
129
Q
A
130
Q
A
131
Q
A
132
Q
A
133
Q
A
134
Q
A
135
Q
A
136
Q
A
137
Q
A
138
Q
A
139
Q
A
140
Q

True or False:

During elimination reactions, the nucleophile acts as a base

A

True

141
Q

What is the rate of an E1 reaction determined by?

A

Concentration of alkyl halide only

142
Q

What is the rate of an E2 reaction determined by?

A

Concentration of the base and the alkyl halide

143
Q

Zaitsev rule states that the more substituted alkene product is obtained when?

A

When a proton is removed from the β-carbon that is bonded to the fewest hydrogens

144
Q

Why are E-alkenes usually lower in energy?

A

Due to steric reasons

145
Q

Why can multiple products be produced in E2 reactions?

A

Often there are 2 β-carbons with hydrogens that could be targeted by the base

146
Q

True or False:

E2 eliminations have anti-periplanr transition states

A

True

147
Q

True or False:

Both E1 and E2 always favour the formation of the more substituted alkene

A

False;

E1 reactions give the more substitutened alkene

E2 reactions give the more substituted alkene, but are regioselective for the less substituted alkene if a hindered base is used

148
Q

Is ΔS higher for elimination or substitution reactions?

A

Elimination (2 become 3; whereas in substitution 2 become 2)

149
Q

Markovnikov’s rule states that the hydrogen ends up attached to the carbn of the double bond that has what?

A

Had more hydrogens to start with

150
Q
A

CHM2911 (4 decks)

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