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CHM 110 > Chapter 7 > Flashcards

Chapter 7 Flashcards

(50 cards)

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1
Q

Which is stronger, CH or CX bonds?

A

CH

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2
Q

Where does the dipole point in CX

A

towards the halogen (negative sigma charge)

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3
Q

Chlorofluorocarbons (CFC’s)

A
  • Widely used as nontoxic heat transfer agents (coolants in AC)
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4
Q

What type of reaction is halogenating an alkane

A

substitution reaction

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5
Q

Polarizability

A

measure of distortion of e- density about the atom

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6
Q

As polarizability increases

A

So does BP (MW is also higher)

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7
Q

Nucleophilic substitution definition

A

the replacement of a group by an incoming nucleophile

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8
Q

What is the leaving group known as

A

electrophile

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9
Q

Nucleophile loves:

A

nucleus (positive charge)

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10
Q

electrophile loves

A

e- (Negative charge)

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11
Q

Common nucleophiles

A

salts of nucleophilic anion

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12
Q

common electrophiles

A

SP3 hybridized alkyl halides

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13
Q

Nucleophile properties

A
  • Negatively charged are best
  • any atom with a lone pair could be a nucleophile
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14
Q

Least to most reactive leaving groups

A

the weaker the bond, the more reactive the leaving group

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15
Q

Walden inversion

A

the inversion of the configuration of a chiral center in a molecule

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16
Q

which reactions do Walden inversions occur?

A

SN2

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17
Q

SN2 reactivity trend

A

Tertiary carbons are the least reactive while Primary carbons are the most reactive (less hindered)

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18
Q

Are anions always needed as nucleophiles

A

No, but they are the best nucleophiles

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19
Q

Nucleophilicity

A

is a particular nucleophile strength at attacking an electrophile

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20
Q

SN1 reaction rate dependent on

A

electrophile concentration only

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21
Q

SN2 reaction rate dependent on

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A

Electrophiles and nucleophile equally important

22
Q

Carbocation stability of SN1

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A

tertiary are most stable, methyl are least stable (rate increases with stability)

23
Q

stereochemistry of SN1

Study These Flashcards
A

Racemates (mixtures) are formed from reactions

24
Q

Why do racemates form In SN1

Study These Flashcards
A

carbocation intermediate is planar and can be “attacked” from the top or bottom face

25
What happens if SN1 or E1 reactions involve carbocations
They will rearrange to form a more stable cation if possible
26
Best type of Solvent for SN2
polar aprotic solvents
27
Aprotic solvents
lack an OH or NH2 group and therefore do not stabilize cations/ anions
28
Nonpolar solvents (SN2)
are not good at solubilizing substrates
29
Tosylates are
great leaving groups
30
Kinetics of SN1
1st order rxn in alkyl halide 1st order rxn in nucleophile Rate dependent on haloalkane and it's rate of disappearance
31
3 requirements for nucleophile substitution to occur
- SP3 central atom - a nucleophile - 1g bonded to central atom ???????
32
What makes a group a good nucleophile
its looking for a base with lone pair and is not sterically restricted
33
what makes a good leaving group
weak base with conj acid having a low PKA
34
SN1 prefers which solvent
polar protic (uses as nucleophile)
35
SN2 prefers which solvent
polar aprotic solvent
36
relationship between SN1 and SN2
They are competing reactions
37
degrees of saturation prefered by SN1
the more the better (secondary and tertiary
38
Degrees of substitution perferred by SN2
primary/ secondary groups
39
Nucleophicity of SN1
poor
40
Nucleophicity of SN2
Good
41
Nucleophilicity trend
The less tightly held the shell is the higher the nucleophilicity is
42
relationship between base strength and nucleophilicity
the more basic (lower PKA), the better the nucleophile
43
structure of haloalkane SN1
electronic factors
44
structure of haloalkane SN2
steric factors (sensitive to hindrance)
45
What happens if nucleophile is solvated well with a protic solvent
The rxn will slow
46
What happens if nucleophile is solvated well with aprotic solvents
rxn will be as fast as the nucleophile allows
47
solvent effect on SN1
separation of opposite charged
48
SN1 polar solvents
solvate both anions and cations
49
How many steps does SN1 have?
2, a carbocation intermediate is formed
50
how many steps in SN2
1

CHM 110 (9 decks)

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