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Organic Chemistry > Ch. 6 > Flashcards

Ch. 6 Flashcards

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1
Q

Alkyl Halides are _____ leving groups and ______ nucleophiles with the exception of ______SN1

A

great
great
Fluorine

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2
Q

Do vinyl halides do SN1, SN2, or neither

A

Neither

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3
Q

Do aryl halides do Sn2, SN1 or neither

A

Neither

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4
Q

Nomenclature (Halogens)

A
  1. Find the longest carbon chain, even if the halogen is not bonded to any of those carbons
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5
Q

Geminal dihalide

A

The two halogens are bonded to the same carbon

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6
Q

Vicinal dihalide

A

The two halogens are bonded to adjacent carbons

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7
Q

What two properties indicate higher boiling points

A

Greater mass, greater intermolecular forces

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8
Q

Spherical shape ______ boiling point

A

decreases

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9
Q

Which halogens are denser than water

A

Alkyl chlorides with two or more chlorines
Alkyl bromides
Alkyl iodides
(alkyl fluorides ARE NOT)

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10
Q

When adding Br, remove the ______ CH

A

weakest

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11
Q

Resonance stabilization of a radial makes it ______ to lose an H

A

easier

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12
Q

A radical wants to be on a tertiary/secondary/primary carbon

A

tertiary

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13
Q

Nucleophilic substitution

A

Halide leaving group is replaced by a nucleophile

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14
Q

Elimination

A

Halide leaving group leaves and electrophile removes a H

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15
Q

Nucleophilic substitution requires an _____ hybridized carbon

A

sp3

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16
Q

A good leaving group has a ______ pKa of its conjugate acid

A

Low

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17
Q

Common electrophiles

A

R-Cl, R-OH, R-OH2+, R-H, R-CH3

18
Q

Common leaving groups

A

Cl-, HO-, H2O, H-, CH3-

19
Q

Common nucleophiles/bases

A

Cl-, OH-, H2O, CH3-, NH2, NH3

20
Q

Polar Protic Solvents (Rank F- to I-)

A

Solvates I- best, then Br-, then Cl-, then F-

21
Q

Polar aprotic Solvents (Rank F- to I-)

A

Solvates F- best, then Cl-, then Br-, then I-

22
Q

Sn2 Rate Law

A

Rate = k[Nuc][Elect]

23
Q

SN2 performs a ________ attack

A

backside atack

24
Q

Backside Attack

A

the nucleophile attacks the electrophilic center on the side that is opposite to the leaving group; Inverts stereochemistry

25
Q

SN2 needs a _______ nucleophile/electrophile

A

good

26
Q

What degree of carbon is fastest with Sn2? Which degree doesn’t react? How does steric impact speed

A

1º is faster than 2º
3º doesn’t react
More sterics, slower rate

27
Q

A negatively charged nucleophile is ________ that its neutral counterpart

A

stronger

28
Q

Nucleophilicty _____ from left to right

A

decreases`

29
Q

Nucleophilicity ______ down the periodic table as size and polarizability increase

A

increases

30
Q

What is the polarizability effect?

A

Bigger atoms are more polarizable and better nucleophiles than expected based on pKa alone

31
Q

SN1 Rate Law

A

Rate = k[Electrophile]

32
Q

Which reaction produces both stereoisomers

A

SN1

33
Q

Delete

A

3º > 2º > 1º > Methyl

34
Q

Polar protic solvnts are best for _____. Why?

A

SN1, solvates ions through hydrogen bonding

35
Q

Hammond Postulate

A

The transition state most closely resembles the starting material/product/intermediate that it is closest to in space

36
Q

SN1 can react with ____ nucleophiles, SN2 needs ____ nucleophiles

A

weak
Strong

37
Q

Do Csp2-X halides react?

A

NO!

38
Q

What is a hydride shift? When can it occur?

A

Shift the H atom and 2 electrons in a bond, when it makes an equally or more stable carbocation

39
Q

How many carbons can you move over in a hydride shift?

A

One

40
Q

Which solvent doesnt have any H bonds

A

Polar Aprotie

41
Q

A good nucleophile is a _______ base

A

strong

Organic Chemistry (15 decks)

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