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Organic Chemistry > CH325 exam 1 > Flashcards

CH325 exam 1 Flashcards

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1
Q

What is a nucleophile?

A

group that donates e-

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2
Q

What is an electrophile?

A

group that accepts e-

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3
Q

Addition of a hydride product:

A

convert carbonyl to OH group + H on carbon

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4
Q

addition of a hydride reactants:

A

NaBH4; LiAlH4

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5
Q

What is a reduction reaction?

A

increasing the amount of hydrogens and decreasing the amount of electronegative atoms

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6
Q

what is an oxidation reaction?

A

increase amount of electronegative atoms and decrease the amount of hydrogen atoms

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7
Q

addition of carbon nucleophiles product:

A

alcohols

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8
Q

addition of carbon nucleophiles intermediate:

A

carbanion and metal cation

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9
Q

addition of carbon nucleophiles reactants:

A

organometallic compounds (metal on a carbon molecule)

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10
Q

acetylide reaction product:

A

OH-C-C—C-R

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11
Q

acetylide reaction reactants:

A

negatively charged alkyne + ketone

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12
Q

addition of hydrogen cyanide product:

A

cyanohydrin (OH-C-CN)

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13
Q

addition of hydrogen cyanide reactants:

A

ketone and HCN

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14
Q

addition of water products:

A

OH-C-OH

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15
Q

addition of water reactants:

A

ketone and OH or H+

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16
Q

addition of alcohols product:

A

OH-C-OR

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17
Q

addition of alcohols reactant:

A

ketone and R-OH and H+

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18
Q

addition of hydrogen halides reactants:

A

alkene and H-X

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19
Q

addition of hydrogen halides product:

A

H-C-C-X (alkene breaks)

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20
Q

What is Markovniks Rule?

A

rich get richer (H atom attaches to the C with more H/less subs.)

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21
Q

acid catalyzed hydration reactants:

A

alkene and H2O

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22
Q

acid catalyzed hydration products:

A

H-C-C-OH

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23
Q

addition of alcohol with acid as a catalyst reactants:

A

alkene and ROH and H+

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24
Q

addition of alcohol with acid as a catalyst product:

A

ether

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25
Q

addition of halogen in an invert solvent reactants:

A

alkene and X2

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26
Q

addition of halogen in an invert solvent products:

A

X-C-C-X (anti addition)

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27
Q

halohydrin formation reactants:

A

alkene and H20 and X2

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28
Q

halohydrin formation product:

A

X-C-C-OH

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29
Q

where does the halogen attach in halohydrin formation?

A

to the C with more H atoms

30
Q

oxymercuration reduction reactants:

A

alkene and Hg(OAc)2 and H20 and NaBH4 and NaOH [2 step rxn]

31
Q

oxymercuration reduction products:

A

H-C-C-OH

32
Q

oxymercuration reduction intermediate:

A

meconium ion

cyclopropane with Hg-OAc as one of the corners

33
Q

epoxidation reactants:

A

alkene and peroxy acid

34
Q

what is peroxy acid?

A

R-COOH

35
Q

epoxidation product:

A

cyclopropane with O in one corner

36
Q

alkene hydroboration oxidation reactants:

A
37
Q

alkene hydroboration oxidation product:

A
38
Q

catalytic hydrogenation reactants:

A

alkene and H+ and Pt (or Pd)

39
Q

catalytic hydrogenation product:

A

H-C-C-H

40
Q

Addition to conjugated dienes reactants:

A

C=C-C=C and HX

41
Q

addition to conjugated dienes product:

A

CH-C(X)-C=C

CH-C=C-C(X)

42
Q

what is the product of a conjugated diene reaction at high temp?

A

1,4 addition

43
Q

addition of hydrogen halides to alkynes reactants:

A

alkyne and HX

44
Q

addition of hydrogen halides to alkynes product:

A

X-C=CH2

45
Q

addition of water to alkyne reactants:

A

alkyne and H2O and H+

46
Q

addition of water to alkyne products:

A

C-C(OH)=CH2

47
Q

alkyne oxymercuration reduction reactants:

A

alkyne and Hg 2+ and H2O and H2SO4

48
Q

alkyne oxymercuration reduction product:

A

C-C(OH)=CH2

49
Q

alkyne hydroboration oxidation reactants:

A

internal alkyne: BH3, THF, H2O, NaOH
terminal alkyne: R2BH, H2O, NaOH

50
Q

alkyne hydroboration oxidation products:

A

internal alkyne: ketone
terminal alkyne: aldehyde

51
Q

addition of Br2 to alkynes reactants:

A

alkyne and Br2

52
Q

addition of Br2 to alkynes products:

A

Br-C=C-Br

53
Q

catalytic hydrogenation reactants:

A

alkyne +
- Pd, H2
- Lindler, H2
- Na or Li, NH3

54
Q

catalytic hydrogenation product for Pd,H2:

A

C-C (both have two H atom on them)

55
Q

catalytic hydrogenation product for Lindlar, H2:

A

alkane with syn addition

56
Q

catalytic hydrogenation product for Na/Li, NH3:

A

alkane with anti addition

57
Q

what is the stereochemistry of an SN2 reaction?

A

Nu back attack, remaining three groups ‘flip’ to other side

58
Q

What happens to the strength of a Nu when the size of them molecule increases?

A

strength increase

59
Q

What happens to the strength of the Nu when the electronegativity increases?

A

strength decreases

60
Q

What is true of the strength of a negatively charged Nu?

A

increased strength

61
Q

What happens to Nu strength when the steric bulk decreases?

A

increased strength

62
Q

What type of reaction doesn’t have good Nu present?

A

SN1

63
Q

What is the mechanism of reaction for an SN1 reaction?

A

bond breaking between electrophilic C and the LG is complete before bond with Nu is formed

64
Q

what is the first step in an SN1 reaction?

A

ionize the C-X bond to get carbocation intermediate

65
Q

What is step two of an SN2 reaction?

A

react carbocation with Nu to get product

66
Q

What type of solvents are involved in an SN2 reaction?

A

polar aprotic

67
Q

What type of solvents are involved in an SN1 reaction?

A

polar protic

68
Q

What are the steps to determine SN1 vs SN2 reactions?

A
  1. structure of substrate
  2. strength of Nu
  3. solvent used

in that order ^^

69
Q

Structure of substrates:

A

SN1: 3º > 2º > 1º > CH3
SN2: CH3 > 1º > 2º > 3º

70
Q

What is the stereochemistry of SN2?

A

inverse

Organic Chemistry (4 decks)

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