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Organic chemistry > Exam 2 Sigman > Flashcards

Exam 2 Sigman Flashcards

1
Q

Pka H2O

A

15.5

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2
Q

Pka NH4+

A

9

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3
Q

Pka Carboxylic acid

A

4.8

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4
Q

Pka alcohol (ROH)

A

16

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5
Q

Pka ROH2+

A

-2 to -5

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6
Q

Pka Ketone

A

19.2

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7
Q

Pka Alkyne

A

25

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8
Q

Pka Ester

A

20-25

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9
Q

Pka Amide

A

25-30

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10
Q

Pka Benzene

A

43

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11
Q

Pka Alkane

A

50

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12
Q

How do you put a Cl on a Benzene

A

Cl2 and FeCl3

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13
Q

How do you put a Br on a benzene?

A

Br2 and FeBr3

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14
Q

How do you put a nitro group (-NO2) on a benzene?

A

HNO3 and H2SO4

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15
Q

How do you put a carbon (R group) on a benzene

A

R-Cl and AlCl3

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16
Q

How do you put a carbonyl group on a Benzene?

A

RCOCl (Acid Chloride) and AlCl3

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17
Q

What is the Clemmenson Reagent?

A

Zn (Hg) and HCl

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18
Q

What does the Clemmenson reagent do?

A

It is a “ketone eraser” so it put’s two Hydrogens instead of the C=O

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19
Q

How do you put a sulfur group on a benzene?

A

SO3 and H2SO4

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20
Q

Alkene + KMnO4, H2O, -OH

A

Syn addition of -OH. Creation of a 1,2 diol

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21
Q

Alkene + 1. O3, 2. Zn, H2O, CH3SCH3

A

Aldehyde + Aldehyde
Ketone + Ketone
Or
Ketone + Aldehyde

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22
Q

Internal Alkyne + 1. O3, 2. H2O

A

2 Carboxylic Acids

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23
Q

Terminal Alkyne + 1. O3, 2. H2O

A

Carboxylic Acid and CO2

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24
Q

Primary Alcohol + PCC

A

Aldehyde

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25
Q

Primary Alcohol + Jones (CrO3, H2SO4, H2O)

A

Carboxylic Acid

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26
Q

Secondary Alcohol + PCC or Jones

A

Ketone

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27
Q

Ph-CH2-R + KMnO4

A

Carboxylic Acid as long as there is one CH before the R

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28
Q

Alkene + O3 and H2O2

A

2 Carboxylic Acids

29
Q

Rank aldehydes, ketones and esters reactivity to nucleophilic attack

A

Aldehydes>Ketones>Esters

30
Q

Aldehyde + LAH, H2O

A

Primary Alcohol

31
Q

Ketone + LAH, H2O

A

Secondary Alcohols

32
Q

Aldehyde + NaBH4, MeOH

A

Primary Alcohol

33
Q

Ketone + NaBH4, MeOH

A

Secondary Alcohol

34
Q

Acid Chloride + LAH, H2O

A

Primary Alcohol

35
Q

Acid Chloride + DIBAL-H, H2O

A

Aldehyde

36
Q

Ester or Carboxylic Acid + LAH, H2O

A

Primary Alcohol

37
Q

Ester + DIBAL-H, H2O

A

Aldehyde

38
Q

Amide + LAH, H2O

A

Amine

39
Q

Aldehyde + JONES

A

Carboxylic Acid

40
Q

How do you make R-Li?

A

R-X + 2Li

41
Q

How do you make a Grignard (R-MgX)?

A

R-X + Mg in Diethyl Ether

42
Q

How do you make a cuprate?

A

2R-Li + CuI

43
Q

Organometallic Reagent + H-O-H(R)

A

R-H + M + -OR

44
Q

Aldehyde or Ketone + R-Li or R-MgX, H2O

A

Primary, Secondary, or Tertiary Alcohols

45
Q

Ester + 2 equivalents of R-Li or R-MgX, H2O

A

Tertiary Alcohol

46
Q

Acid Chloride + 2 equivalents of R-Li or R-MgX, H2O

A

Tertiary Alcohol

47
Q

Acid Chloride + R2CuLi, H2O

A

Ketone

48
Q

R-MgX + CO2 (Acidic work up)

A

Carboxylic Acid

49
Q

Epoxide + R-M, H2O

A

Epoxide opens the less substituted side

50
Q

Alpha, beta unsaturated carbonyl + R-MgX or R-Li, H2O

A

1,2 Addition

51
Q

Alpha Beta unsaturated carbonyl + R2CuLi, H2O

A

1,4 Addition

52
Q

What is a good protecting group for Alcohol?

A

Silyl Chloride and Imidazole

53
Q

How do you take off the protecting group for alcohol?

A

TBAF

54
Q

Ketone + NaCN, HCl

A

H and CN add across the carbonyl bond. RCOHRCN

55
Q

Aldehyde + NaCN, HCl

A

H and CN add across the carbonyl bond.

56
Q

Ketone + Wittig Reagent

A

Alkene (substituted according to how substituted the starting materials were)

57
Q

Aldehyde + Wittig Reagent

A

Alkene (substituted according to how the starting materials were substituted.)

58
Q

NaBH4 will only add a nucleophilic hydride to a carbonyl carbon. True or False?

A

True

59
Q

1 equivalent of H2 and Pd/C will add hydrogen across an Alkene but not a carbonyl. True or False?

A

True

60
Q

2 equivalents or more of H2, Pd/C will reduce both the carbonyl bond and the Alkene. True or False?

A

True and it will make a secondary alcohol.

61
Q

What type of reaction does NADH do?

A

It donates a nucleophilic hydride to the carbonyl carbon and then the alkoxide oxygen grabs a proton from water.

62
Q

Internal or External Alkyne + 1. BH3 2. H2O2, -OH

A

Aldehyde or Ketone depending upon starting material

63
Q

External Alkyne + 1. H2O, 2. H2SO4, HgSO4

A

Ketone

64
Q

You see a carbonyl and a strong acid…what is going to happen first?

A

The carbonyl oxygen is going to be protonated. Acid-Base Chemistry.

65
Q

Aldehyde or Ketone + RNH2 and mild acid

A

Imine (C=N-R)

66
Q

Aldehyde or Ketone + R2NH and mild acid

A

Enamine (C=C-NR2)

67
Q

Aldehyde or Ketone + H2O and Acidic/Basic

A

Gem-Diol

68
Q

Aldehyde or Ketone + 2 equivalents of ROH and Acidic work up

A

Acetal + H2O

69
Q

Pka strong acid (H2SO4, HCl, HBr, HI, HNO3

A

-9

Organic chemistry (6 decks)

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