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Organic Chemistry > 7-Aklyl Halides and Nucleophilic Substitution > Flashcards

7-Aklyl Halides and Nucleophilic Substitution Flashcards

1
Q

boiling point of alkyl halides (increase/decrease) as the size of R increases

A

INCREASE

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2
Q

Melting point of alkyl halides (increase/decrease) as the size of R increases

A

INCREASE

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3
Q

Boiling point of alkyl halides (increase/decrease) as the size of
X increases

A

increase

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4
Q

Melting point of alkyl halides (increase/decrease) as the size of X increases

A

increase

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5
Q

alkyl halides are (insoluble/soluble) in organic solvents

A

soluble

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6
Q

alkyl halides are (insolble/insoluble) in water

A

insoluble

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7
Q

alkyl halides undergo ______ reactions with NUCLEOPHILES

A

substitution

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8
Q

alkyl halides undergo ______ reactions with BRONSTED-LOWRY BASES

A

elimination

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9
Q

The better leaving group is the (weaker/stronger) base

A

weaker

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10
Q

across a row, basicity (increases/decreases)

A

decreases

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11
Q

across a row, leaving group ability (increases/decreases)

A

increases

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12
Q

Down a column, basicity (increases/decreases)

A

decreases

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13
Q

Down a column, leaving group ability (increases/decreases)

A

increases

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14
Q

Good leaving groups have (high/low) pKa

A

low

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15
Q

When the leaving group is a weaker base than the nucleophile the (reactants/products) are favored?

A

products

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16
Q

Nucleophiles normally attack?

A

carbons

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17
Q

nucleophilicity (increases/decreases) as basicity (increases/decreases)

A

increase-increase or decrease-decrease

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18
Q

As the number of R groups on the carbon with the leaving group increases, the rate of the SN2 reaction (increases/decreases)

A

decreases

19
Q

Rate of SN2 reactions (substitution of R group)

A

(fastest)CH3-X > RCH2-X > R2CH-X > R3C-X (slowest)

20
Q

SN2 Mechanism

kinetics

A

second order

rate=k[RX][Nu:-]

21
Q

SN2 Mechanism

mechanism

A

one step

22
Q

SN2 Mechanism

stereochemistry

A

backside attack of the nucleophile

inversion of configuration at a stereogenic center

23
Q

SN2 Mechanism

identity of R and rate

A

CH3-X > RCH2X > R2CHX > R3CX

24
Q

SN2 reactions have ___ step(s)

A

one

25
Q

SN1 reactions have ___ step(s)

A

two

26
Q

______ are formed as a reactive intermediate in an SN1 reaction

A

cabocations

27
Q

As the number of R groups on the carbon with the leaving group increases, the rate of the SN1 reaction (increases/decreases)

A

increases

28
Q

Rate of SN1 reactions (substitution of R group)

A

(slowest) CH3-X < RCH2-X < R2CH-X < R3C-X(fastest)

29
Q

SN1 Mechanism

kinetics

A

first order

rate=k[RX]

30
Q

SN1 Mechanism

mechanism

A

two steps

31
Q

SN1 Mechanism

stereochemistry

A

trigonal planar carbocation intermediate

racemization at a single stereogenic center

32
Q

SN1 Mechanism

identity of R and rate

A

R3CX > R2CHX > RCH2X > CH3X

33
Q

carbocation stability

A

(least stable)CH3 < RCH2 < R2CH < R3C(most stable)

34
Q

Vocab:

spreading our charge by the overlap of an empty p orbital with an adjacent sigma bond is called

A

hyperconjugation

35
Q

as alkyl substitution increases, dispersal of positive charge (increases/decreases)

A

increases

36
Q

rate of an SN1 reaction (increases/decreases) as the stability of the carbocation (increases/decreases)

A

increase-increase or decrease-decrease

37
Q

increasing alkyl substitution favors ___

A

SN1

38
Q

decreasing alkyl substitution favors ___

A

SN2

39
Q

strong nucleophiles favor (SN1/SN2)

A

SN2

40
Q

weak nucleophiles favor (SN1/SN2)

A

SN1

41
Q

SN1 reactions favor polar (protic/aprotic) solvents

A

protic

42
Q

SN2 reactions favor polar (protic/aprotic) solvents

A

aprotic

43
Q

solvent that contains an O-H or N-H bond

A

polar protic

44
Q

solvent does NOT contain an O-H or N-H bond

A

polar aprotic

Organic Chemistry (6 decks)

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