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organic chemistry 1 > exam 2 content > Flashcards

exam 2 content Flashcards

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1
Q

Methyl carbon

A

only SN2

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2
Q

primary C, with (KOTBU)

A

E2 elimination, Hoffman’s rule

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3
Q

primary C, NaCL

A

SN2 reaction

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4
Q

If an SN2 reaction occurs, and the C is chiral what happens?

A

stereochemistry flips

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5
Q

secondary C, STRONG and LARGE base (KOTBu)

A

E2 reaction, Hoffman’s rule

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6
Q

Secondary C, strong small base (NaOH, NaOME, NaOET)

A

E2, zaitsev

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7
Q

secondary C, “neutral” base (H2O, ETOH), low temperature

A

SN1

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8
Q

if an SN1 reaction has chirla C it forms what

A

racemic mixtures

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9
Q

secondary C, “neutral” base (h2o, etoh), high temperature

A

E1, zaitsev

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10
Q

Secondary C, weak basic Nu (CI, Br, CH3COO, CN, N3)

A

sn2

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11
Q

tertiary C, Strong base (NaOME/NaOET)

A

e2 zaitsev

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12
Q
A
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13
Q

Tertiary C, Strong base (KOTBU)

A

e2 hoffman

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14
Q

Tertiary C, Neutral Base, low temperature

A

SN1

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15
Q

Tertiary C, neutral base, high temperature (MeOH/ETOH)

A

E1 reaction zaitsev

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16
Q

list the good leaving groups/ extremely weak bases

A

TsO, MsO, TfO, H2O, Tf2O

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17
Q

will stereochemistry change with Sulfonates?

A

NO, to change stereochemistry, put things through an SN2 reaction.

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18
Q

phosphorous loves ____

A

Oxygen

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19
Q

water/ ETOH

A

SN1 solvents

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20
Q

I, Br, CH#COO, CN, N3

A

SN2 nucleophiles

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21
Q

Clock wise priority

A

R

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22
Q

Counterclockwise priority

A

S

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23
Q

If the higher priorities are on the same side

A

Z

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24
Q

If the higher priorities are on opposite sides

A

E

25
Q

What do Nikoxides do?

A

Form double bonds in a molecule by breaking other bonds.

26
Q

Name all Nikoxides

A

NaoME, NaOCH3, NaOET, NaOCH2CH3, KotBu, Kot

27
Q

What is zaitsev’s rule?

A

the most stable will be the major product. (note stability of double bonds)

28
Q

what is hoffmans rule?

A

least substituted will be formed.

29
Q

what follows hoffmans rule?

A

KotBu

30
Q

what follows Zaitsev’s rules?

A

NaOMe, NaOCH3, NaOET, NaOCH2CH3

31
Q

What does catalytic H2SO4 do?

A

Rearrangement, it will take the atom off and form a carbo cation, a shift will occur (methyl, hydride, or ring expansion), and then Oh2 will come back in and form rearrangement.(examples on pg 20 of notes)

32
Q

hydride shift

A

taking a hydrogen, moving it to the carbocation, and then breaking that bond to form a double bond from excess H2O.

33
Q

Methyl Shift

A

removing the group to make a cation, then moving a methyl group to the site, then taking the invisible H and forming a double bond where needed.

34
Q

Ring expansion

A

Removing group to form cation, then expanding the ring to the cation site, take an invisible H and break its bond to form a double bond.

35
Q

Alkyne Recations

A

NaNH2 on top and something on bottom, these should always grow the alkyne.

36
Q

Anti addition

A

double elimination using NaNH2 to become probably an alkyne

37
Q

Syn Addition

A

has a Cis product,

38
Q

how do you get a trans product in syn addition?

A

Li NH3 (liquid) on top, and low temperature

39
Q

anti markovnikov means

A

the poor get rich

40
Q

in order to use Anti-Markovnikov you must use

A

HBr, and Peroxide

41
Q

Markovnikovs rule

A

the rich get richer

42
Q

regio selective

A

one constitutional isomer is favored over the other

43
Q

Hydration reaction

A

Cat HCl, or Cat. H2SO4 over H2O, (really H3O) and add an alcohol to the most substituted site.

44
Q

Carbocation Rearrangement

A

Oh is in the most stable place.

45
Q

Oxymercuration-demurcuration

A

NaBH4

46
Q

Oxymercuration-demurcuration

A

adding an OH group to stable sight.

47
Q

If H2O is replaced in an Oxymercuration-demercuration reaction, how will the product react?

A

instead of an OH group, an OMe group will be placed.

48
Q

what is the difference between Syn and Anti addition

A

The addition of two substituents to the same side of an unsaturated molecule is known as syn addition. The addition of two substituents in opposite directions is known as anti-addition.

49
Q

Hydroboration

A

H2O, NaOH, H2O

50
Q

what does hydroboration do?

A

gives an OH group to the least substituted site, the exact opposite of oxymercuration, de-mercuration.

51
Q

what is a carbene?

A

lone pair, P orbital, and 2 H’s on a C

52
Q

Oxidation

A

gain O or lose H

53
Q

Reduction

A

lose O or gain H

54
Q

1,2 diol syn addition

A

two OH groups are added to the same face.

55
Q

Oxidation of alkenes

A

NaHSO3, H2O

56
Q

Cold basic (COld KMnO4/ NaOH, H2O)

A

does the same as OSO4 in oxidation of alkenes

57
Q

Hot acidic (Hot HMnO4/ H3O)

A

cleaves double bonds/unravels things.

58
Q

for hot acidic KMnO4, what do you add depending on H number on C

A

0H, ketone
1H, carboxylic acid
2H, CO2

59
Q
A

organic chemistry 1 (2 decks)

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