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Chemistry > Alkyl Halides > Flashcards

Alkyl Halides Flashcards

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1
Q

Reactivity of alkyl halides depend on

A

Bond energy, polarity (more = more reactive) and bond length

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2
Q

What is the hybridization of alkyl halides?

A

sp3

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3
Q

C-Cl bond length in alkyl halide

A

178 pm

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4
Q

Alkyl halide bond angle

A

109.5º

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5
Q

Down the group, H-X reactivity

A

Increases

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6
Q

H-X reactivity order

A

HI > HBr > HCl > HF

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7
Q

The __ -carbon of alkyl halides is _____philic in nature

A

alpha-carbon is electrophilic in nature

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8
Q

Halogen atom is a good __________ group

A

Leaving group

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9
Q

The elimination reaction (dehydrohalogenation) of an alkyl halide gives an

A

Alkene

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10
Q

The bond energy of HI is

A

228 kJ/mol

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11
Q

The molecule undergoing nucleophilic reaction is called the

A

Substrate

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12
Q

The group leaving the substrate/being replaced is called the

A

Nucleofuge

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13
Q

Any species ________ or ___________ with an unshared pair of e- can act both as a base and a nucleophile

A

Neutral or negatively charged

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14
Q

A nucleophile undergoes _________________ reactions

A

Nucleophilic substitution or addition reactions

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15
Q

Bases give __________ reactions

A

Elimination reactions

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16
Q

The positive carbon of alkyl carbocation is ____ hybridized and therefore has a __________ structure

A

sp2 and trigonal planar structure

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17
Q

Alkyl groups are electron _______

A

Donating

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18
Q

Carbocation stability order

A

Tertiary carbocation > Secondary carbocation > Primary carbocation > Methyl carbocation
(Most stable) (Least stable)

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19
Q

Unimolecular substitution is ______ and _____ step mechanism

A

Unimolecular and two step mechanism

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20
Q

SN1: First step is

A

Slow / rate determining

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21
Q

SN1 mechanism is followed by

A

Tertiary alkyl halides

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22
Q

SN1 mechanism is favored by ______ solvents (having _______ bonds)

A

Highly ionizing polar solvents (Polar protic). (having O-H , N-H bonds)

23
Q

SN1 has ______ nucleophile and _____ leaving group

A

Weak nucleophile and good leaving group

24
Q

SN1 follow _____ order kinetics

A

First order kinetics

25
Q

If nucleophile attacks carbocation from the side of the leaving group, the product shows _______ of configuration.
If nucleophile attacks carbocation from the opposite side, the product shows _______ of configuration.

A

Side = Retention
Opposite = Inversion (O and I are both vowels)

26
Q

Racemic Mixture is

A

When reactant is chiral, so a mixture of two enantiomers are produced

27
Q

Racemization is

A

A mixture of retention and inversion

28
Q

In SN1 there is _______ racemization

A

Partial

29
Q

In SN1 there is more _______ than ________

A

Inversion than retention (more opps in SN1)

30
Q

SN2 is _____ and ___ step

A

Bimolecular and one step

31
Q

SN2 is followed by ________

A

Primary carbocations and methyl halides

32
Q

SN2 follows _____ order kinetics

A

Second order kinetics

33
Q

SN2 is favored by _________ solvents

A

Polar aprotic solvents (aprotic means unable to ionize)

34
Q

SN2 goes thru _______ of configuration

A

Inversion only

35
Q

Secondary alkyl halides follow SN1 if __________, and SN2 if _______

A

SN1 if polar protic solvent present, SN2 if polar aprotic solvent present

36
Q

In 1,2 elimination, proton is removed from ___ position and halide is removed from ____ position

A

Proton from Beta, Halide from Alpha position

37
Q

SN2 has a ____ nucleophile and a ____ leaving group

A

Strong nucleophile and bad leaving group

38
Q

Which leaves first in 1,2 elimination

A

Beta first then alpha

39
Q

E1 is ____ and _______

A

Unimolecular and two steps

40
Q

E1 is followed by _____ alkyl halides

A

Tertiary

41
Q

E1 follows _____ order kinetics

A

First

42
Q

E1 has a ____ base

A

Weak base

43
Q

E1 needs _______ solvents

A

Polar protic solvents

44
Q

E2 is ___ and _____ step

A

Bimolecular and one step

45
Q

E2 follows ___ order kinetics

A

Second

46
Q

E2 prefers ______ solvents

A

Polar aprotic solvents

47
Q

E2 has a _____ base

A

Strong base

48
Q

E2 is followed by _____ alkyl halides

A

Primary

49
Q

Crowding around alpha carbocation generally favors _____ over _______. This is due to _______

A

Elimination over substitution. This is due to greater steric hindrance

50
Q

The greater number of alkyl groups favors _____ over ______

A

Elimination over substitution

51
Q

A stronger base will favor _____ and a stronger nucleophile will favor _______

A

Base will favor elimination and nucleophile will favor substitution

52
Q

2bromo propane with ethoxide ion (C2H5O-) vs with ethanthiolate ion (C2H5S-)

A

Ethoxide ion = Elimination
Ethanthiolate ion = Substitution

53
Q

Order from strongest nucelophiles to strongest bases

A

I-, HS-, RS- > Br-, OH-, OR-, CH- > Cl, F, NH3, RCOO- > H2O, ROH
Strongest Weakest (but Strongest
Nucleophile Nucleophile Base)

Chemistry (17 decks)

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