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orgo chem > ch.7 > Flashcards

ch.7 Flashcards

1
Q

Sn2

A

nucleophilic attack, loss of a leaving group

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2
Q

methyl

A

3 hydrogen attached to alpha carbon

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3
Q

primary 1

A

2 hydrogen attached to alpha carbon

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4
Q

secondary 2

A

1 hydrogen attached to alpha carbon

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5
Q

tertiary 3

A

no hydrogens attached to alpha carbon

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6
Q

strong nucleophiles

A

I, BR, Cl, HS, RS, HO, RO, CN

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7
Q

weak nucleophiles

A

H2O, ROH

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8
Q

Sn2 preferred solvent.

A

polar aprotic

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9
Q

protic solvents

A

water, methanol, ethanol, ammonia, acetic acid

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10
Q

polar aprotic solvents

A

Acetone, Dimethylsulfoxide (DMSO), Dimethylformamide (DMF), acetonitrile, Hexamethylphosphoramide (HMPA)

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11
Q

protic solvents

A

H-bonding stabilize anions (like good nucleophiles) and also cations

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12
Q

Aprotic solvents

A

stabilize cations only

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13
Q

E2

A

proton transfer, loss of a leaving group

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14
Q

Sn1

A

lose of a leaving group, nucleophilic attack (proton transfer)

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15
Q

E1

A

loss of leaving group and proton transfer

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16
Q

strong base; weak nucleophile (1-3)

A

E2

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17
Q

strong base; strong nucleophile 1

A

E2 minor, Sn2 major

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18
Q

strong base; strong nucleophile 2

A

E2 major; Sn2 minor

19
Q

strong base; strong nucleophile 3

A

E2

20
Q

weak base; strong nucleophile (1-2)

A

Sn2

21
Q

weak base; strong nucleophile 3

A

Sn1

22
Q

weak base; weak nucleophile (sterically hindered) 3

A

E1

23
Q

weak base; weak nucleophile (non-sterically hindered) 3

A

Sn1

24
Q

most stable to least stable carbocations

A

tertiary>secondary>primary>methyl

25
Q

least reactive to most reactive

A

I>Br>Cl>F

26
Q

water solvent type

A

protic

27
Q

ethanol solvent type

A

protic

28
Q

ammonia solvent type

A

protic

29
Q

acetic acid solvent type

A

protic

30
Q

acetone solvent type

A

polar aprotic

31
Q

DMF solvent type

A

polar aprotic

32
Q

HMPA solvent type

A

polar aprotic

33
Q

DSMO solvent type

A

polar aprotic

34
Q

acetonitrile solvent type

A

polar aprotic

35
Q

what is the major product for a substitution reaction with a sterically hindered substrate and sterically hindered base?

A

the less substituted alkane

36
Q

bredt’s rule

A

a small bicyclo ring cannot have alkenes at the bridgeheads

37
Q

strong bases; weak nucleophiles

A

DBN;DBU

38
Q

strong bases; strong nucleophiles

A

OH-;EtO-;MeO-

39
Q

weak bases, strong nucleophiles

A

I; Br; Cl; RS; HS; RSH;

40
Q

weak bases, weak nucleophiles

A

H2O, MeOH, EtOH

41
Q

what does the rate of an Sn2 reaction depend on?

A

the strength of the nucleophile

42
Q

what does the rate of an E2 reaction depend on?

A

concentration of the alkyl halide and of the base

43
Q

what is the RDS for E1 and Sn1 reactions?

A

loss of a leaving group

orgo chem (3 decks)

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