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Organic Chemistry > Chapter 6 > Flashcards

Chapter 6 Flashcards

1
Q

alkyl halide

A

halogen is directly bonded to an sp3 carbon

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2
Q

vinyl halide

A

halogen is bonded to an sp2 carbon of alkene

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3
Q

aryl halides

A

halogen is bonded to an sp2 carbon on a benzene ring

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4
Q

halogens are ______ electronegative than carbon

A

more

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5
Q

methyl halides

A

halide is attached to a methyl group

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6
Q

primary alkyl halide

A

the carbon to which halogen is bonded, is attached to only one carbon

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7
Q

secondary alkyl halide

A

halogen is attached to a carbon that is secondary

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8
Q

tertiary alkyl halide

A

halogen is attached to a carbon that is tertiary

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9
Q

germinal dihalide

A

two halogen atoms are bonded to the same carbon

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10
Q

vicinal dihalide

A

two halogen atoms are bonded to adjacent carbons

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11
Q

uses of alkyl halides

A
  • industrial and household cleaners
  • anesthetics
  • freons used in refrigerants and foaming agents
  • pesticides
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12
Q

greater intermolecular forces, __________ the boiling point

A

higher

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13
Q

spherical shape _________ boiling point

A

decreases

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14
Q

free radical halogenation

A
  • chlorination = mixture of products
  • bromination = highly selective
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15
Q

free radical allylic halogenation

A

halogen is placed on a carbon directly attached to the double bond

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16
Q

prefix: F

A

fluoro

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17
Q

prefix: Cl

A

chloro

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18
Q

prefix: Br

A

bromo

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19
Q

prefix: I

A

iodo

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20
Q

Alkyl halides have ____ priority when it comes to numbering the direction of the chain

A

NO

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21
Q

when a nucleophile reacts with an electrophile that does not have an empty orbital

A

substitution reaction

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22
Q

in a substitution reaction, we use the _______ of the leaving group to determine reaction rate

A

stability

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23
Q

due to their high electronegativity, _________________ will be the primary leaving groups

A

alkyl halides

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24
Q

increasing carbocation stability

A

1 < 2 < allylic < bensylic < 3

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25
Q

increasing radical stability

A

1 < 2 < 3 < allylic - benzylic

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26
Q

SN2 (full name)

A

substitution nucleophilic bimolecular

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27
Q

SN2 Properties: nucleophile

28
Q

SN2 Properties: leaving group

A

unsubstituted and strong

29
Q

SN2 Properties: reaction coordinate

A

transition state

30
Q

SN2 Properties: concerted or stepwise

31
Q

SN2 Properties: rate

A
  • bimolecular
  • k[Nu][RX]
32
Q

SN2 Properties: stereochemistry

33
Q

SN2 nickname

A

backside attack

34
Q

SN2: order of reactivity

A

methyl > 1 > 2 (tertiary is impossible)

35
Q

the more -R groups, the more substituted the carbocation, the __________ stable

36
Q

SN1 (full name)

A

substitution nucleophilic unimolecular

37
Q

SN1 Properties: nucleophile

38
Q

SN1 Properties: leaving group

A

highly unsubstituted

39
Q

what does substituted mean?

A

more R groups (less H)

40
Q

SN1 Properties: concerted or stepwise

41
Q

SN1 Properties: rate

A
  • unimolecular
  • k[RX]
42
Q

SN1 Properties: stereochemistry

43
Q

SN1 nickname

A

soluolysis (common solvents: H2O, ROH, NH3)

44
Q

polar solvents are solvents which contain a _______________

A

net dipole

45
Q

aprotic polar solvents are solvents that cannot display ______________

A

hydrogen bonding

46
Q

protic solvents are solvents that display _____________

47
Q

Which reactions do we prefer in protic solvents?

A

SN1 and E1

48
Q

Which reactions do we prefer in aprotic solvents?

A

SN2 and E2

49
Q

H2O, -OH, and amines (polar protic or aprotic)

A

polar protic

50
Q

THF, DMSO, DMF, (other achronyms) –> (polar protic or aprotic)

A

polar aprotic

51
Q

alcohol is __________ with a strong acid as it is a common leaving group

A

protonated

52
Q

-OTs

A

Sulfonate Ester –> Tosyl (benzene and methyl)

53
Q

-OMs

A

Sulfonate Ester –> Mesyl (methyl group)

54
Q

-OTf

A

Sulfonate Ester –> Triflyl (CF3)

55
Q

molecule that can easily donate electrons

A

nucleophile

56
Q

molecule that can easily remove a proton

57
Q

a negative charge will always be a ___________ nucleophile than its neutral counterpart

58
Q

the bulkier the substrate, the more ______ and less _________ it is

A

basic, nucleophilic

59
Q

better size for a better base / nucleophile

60
Q

Nucleophilicity in ________ solvents increases as the size of the atom increases.

61
Q

carbocations are stabilized by a phenomenon called _______________

A

hyperconjucation (adjacent sigma bonds can share electron density with the carbocation)

62
Q

the more substituted the carbocation, the more _______________

A

stable (1 < 2 < allylic - benzylic < 3)

63
Q

1, 2 hydride shift

A

occurs when there is a hydrogen located on an adjacent, more stable carbon

64
Q

1,2 alkyl shift

A

occurs when only small alkyl groups are located on an adjacent, more stable carbon

65
Q

ring expansion occurs only on what size of membered ring?

A

2, 3 or 5 membered ring ONLY

Organic Chemistry (9 decks)

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