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CHM2911 > Organic Chemistry I > Flashcards

Organic Chemistry I Flashcards

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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
# Define Oxymecuration
an electrophilic addition organic reaction that transforms an alkene into a neutral alcohol
26
# Define Radical
an atom, molecule, or ion that has an unpaired valence electron
27
# Define Reactive intermediates
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
28
# Define Rearrangment reactions
a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule
29
# Define Regioselectivity
the preference of one direction of chemical bond making or breaking over all other possible directions
30
# Define Second-order reaction
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
31
# Define SN1 reaction
A reaction in which a Nucleophile Substitutes for a leaving group. It goes through a carbocation intermediate
32
# Define SN2 reaction
reaction is a bimolecular (2 molecules) reaction involving the Substitution of a Nucleophile for a leaving group
33
# Define Sp hybridisation
a type of hybridization where the s orbital overlaps with only one p orbital
34
# Define Sp2 hybridisation
The process of intermixing of one S and two P orbitals to give three identical hybrid orbitals
35
# Define Sp3 hybridisation
refers to the mixing of one s and three p orbitals to form four sp3 hybridized orbitals
36
# Define Stereogenic centre
any location in a molecule where the interchange of any two groups gives a new stereoisomer
37
# Define Stereoselectivity
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
38
# Define Steric effects
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
39
# Define Zaitsev rule
an empirical rule for predicting the favored alkene product(s) in elimination reactions
40
# Definition describes two bonds that are antiparallel in the plane they define (i.e. C-H and C-LG bonds)
Anti-periplanar
41
# 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
Backside attack
42
# Definition Any reaction or process in which bromine (and no other elements) are introduced into a molecule
Bromination
43
# Definition an organic anion in which the negative charge is located on a carbon atom
Carboanion
44
# 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
Carbocation
45
# Definition The geometric property of a rigid object (or spatial arrangement of points or atoms) of being non-superposable on its mirror image
Chirality
46
# Definition A single step mechanism. Describes SN2 and E2 mechanisms
Concerted
47
# 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
E1 reaction
48
# 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
E2 reaction
49
# Definition electrons in a molecule, ion or solid metal that are not associated with a single atom or a covalent bond
Electron delocalisation
50
# 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
Electrophile
51
# Definition a reaction between an electrophile and nucleophile, adding to double or triple bonds
Electrophilic addition
52
# Definition a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism
Elimination reaction
53
# Definition an SN2reaction (Substitution Nucleophilic Bimolecular reaction) that involves the exchange of one halogen atom for another
Finkelstein reaction
54
# Definition a chemical reaction in which the rate of reaction is directly proportional to the concentration of the reacting substance
First-order reaction
55
# 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
Frontside attack
56
# 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
Hybridisation
57
# 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
Hydroboration
58
# 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
Hyperconjugation
59
# Definition a diagram that shows the covalent bonds and lone electron pairs in a molecule
Lewis structure
60
# 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
Markivnikov's rule
61
# Definition Any reaction that introduces a covalent mercury bond into a compound
Mecuriation
62
# 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
Nucleophile
63
# 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
Nucleophilic substitution reactions
64
# Definition an electrophilic addition organic reaction that transforms an alkene into a neutral alcohol
Oxymecuration
65
# Definition an atom, molecule, or ion that has an unpaired valence electron
Radical
66
# 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
Reactive intermediates
67
# 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
Rearrangment reactions
68
# Definition the preference of one direction of chemical bond making or breaking over all other possible directions
Regioselectivity
69
# 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
Second-order reaction
70
# Definition A reaction in which a Nucleophile Substitutes for a leaving group. It goes through a carbocation intermediate
SN1 reaction
71
# Definition reaction is a bimolecular (2 molecules) reaction involving the Substitution of a Nucleophile for a leaving group
SN2 reaction
72
# Definition a type of hybridization where the s orbital overlaps with only one p orbital
Sp hybridisation
73
# Definition The process of intermixing of one S and two P orbitals to give three identical hybrid orbitals
Sp2 hybridisation
74
# Definition refers to the mixing of one s and three p orbitals to form four sp3 hybridized orbitals
Sp3 hybridisation
75
# Definition any location in a molecule where the interchange of any two groups gives a new stereoisomer
Stereogenic centre
76
# 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
Stereoselectivity
77
# 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
Steric effects
78
# Definition an empirical rule for predicting the favored alkene product(s) in elimination reactions
Zaitsev rule
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83
What are the three different types of hybridisation that can occur?
84
How many σ-bonds does sp3 hydridisation have?
4 σ-bonds s1p3: 1+3=4
85
What is the bond angle of an sp2 carbon?
120 degrees
86
In ethene, each C atom has __ sp2 orbital(s) and __ p orbital(s)
In ethene, each C atom has **3** sp2 orbitals and **1** p orbital
87
What is the bond angle of a sp carbon?
180 degrees
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91
What are the two electron deficient states that a carbon molecule can exist in?
Radical and carbocation
92
True or False: Carbocations are electrophilic
True They are electron deficient and therefore seek out more electrons
93
True or False: Carboanions are electrophilic
False They are nucleophilic since they are electron rich
94
Carbocations have __ s and __ p orbitals
Carbocations have **1** s and **2** p orbitals
95
What hybridisation state are carbocations in?
sp2
96
What hybridisation state are carbon centered radicals in?
sp2
97
What hybridisation state are carboanions in?
sp3
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99
When drawing resonance contributors, how can electrons be moved?
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
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103
List the carbocations in order of increasing stability Why is this the case?
3° \> 2° \> 1° \> methyl This is because the charge can be delocalised over a greater number of nuclei
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105
\_\_\_\_\_\_\_\_\_\_\_\_ donate high-energy electrons to electrophiles \_\_\_\_\_\_\_\_\_\_ have a low-energy vacant orbital
**Nucleophiles** donate high-energy electrons to electrophiles **Electrophiles** have a low-energy vacant orbital
106
**\_\_\_\_\_\_\_\_\_\_**are negatively charged or neutral species with a pair of electrons **\_\_\_\_\_\_\_\_\_\_\_\_**are neutral or positively charged species with an empty atomic orbital
**Nucleophiles** are negatively charged or neutral species with a pair of electrons **Electrophiles** are neutral or positively charged species with an empty atomic orbital
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109
What happens in a general nucleophilic substitution reaction?
A nucleophile attacks a sp3 hybridised carbon and the leaving group leaves
110
If a stable carbocation can't form then a *SN1/SN2 (choose one) reaction mechanism is not possible*
If a stable carbocation can't form then a **SN1** *reaction mechanism is not possible*
111
What reaction mechanism is this?
SN1 mechanism
112
What reaction mechanism is this?
SN2 mechanism
113
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 \_\_\_\_\_\_\_\_
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**
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115
What determines the rate of an SN1 reaction?
The concentration of the alkyl halide (if the concentration of the alkyl halide doubles, the rate doubles)
116
What determines the rate of an SN2 reaction?
The rate depends on the concentration of both reagents (if the concentration of the alkyl halide or the nucleophile doubles, the rate doubles)
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122
What type of solvent favours an SN2 reaction?
A polar, aprotic solvent like DMF or DMSO
123
What type of solvent favours an SN1 reaction?
A polar, protic solvent like H2O, R-OH, R-COOH
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140
True or False: During elimination reactions, the nucleophile acts as a base
True
141
What is the rate of an E1 reaction determined by?
Concentration of alkyl halide only
142
What is the rate of an E2 reaction determined by?
Concentration of the base and the alkyl halide
143
Zaitsev rule states that the more substituted alkene product is obtained when?
When a proton is removed from the β-carbon that is bonded to the fewest hydrogens
144
Why are E-alkenes usually lower in energy?
Due to steric reasons
145
Why can multiple products be produced in E2 reactions?
Often there are 2 β-carbons with hydrogens that could be targeted by the base
146
True or False: E2 eliminations have anti-periplanr transition states
True
147
True or False: Both E1 and E2 always favour the formation of the more substituted alkene
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
Is ΔS higher for elimination or substitution reactions?
Elimination (2 become 3; whereas in substitution 2 become 2)
149
Markovnikov's rule states that the hydrogen ends up attached to the carbn of the double bond that has what?
Had more hydrogens to start with
150

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