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Organic chemistry > Exam 2 Sigman > Flashcards

Exam 2 Sigman Flashcards

(69 cards)

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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
Primary Alcohol + Jones (CrO3, H2SO4, H2O)
Carboxylic Acid
26
Secondary Alcohol + PCC or Jones
Ketone
27
Ph-CH2-R + KMnO4
Carboxylic Acid as long as there is one CH before the R
28
Alkene + O3 and H2O2
2 Carboxylic Acids
29
Rank aldehydes, ketones and esters reactivity to nucleophilic attack
Aldehydes>Ketones>Esters
30
Aldehyde + LAH, H2O
Primary Alcohol
31
Ketone + LAH, H2O
Secondary Alcohols
32
Aldehyde + NaBH4, MeOH
Primary Alcohol
33
Ketone + NaBH4, MeOH
Secondary Alcohol
34
Acid Chloride + LAH, H2O
Primary Alcohol
35
Acid Chloride + DIBAL-H, H2O
Aldehyde
36
Ester or Carboxylic Acid + LAH, H2O
Primary Alcohol
37
Ester + DIBAL-H, H2O
Aldehyde
38
Amide + LAH, H2O
Amine
39
Aldehyde + JONES
Carboxylic Acid
40
How do you make R-Li?
R-X + 2Li
41
How do you make a Grignard (R-MgX)?
R-X + Mg in Diethyl Ether
42
How do you make a cuprate?
2R-Li + CuI
43
Organometallic Reagent + H-O-H(R)
R-H + M + -OR
44
Aldehyde or Ketone + R-Li or R-MgX, H2O
Primary, Secondary, or Tertiary Alcohols
45
Ester + 2 equivalents of R-Li or R-MgX, H2O
Tertiary Alcohol
46
Acid Chloride + 2 equivalents of R-Li or R-MgX, H2O
Tertiary Alcohol
47
Acid Chloride + R2CuLi, H2O
Ketone
48
R-MgX + CO2 (Acidic work up)
Carboxylic Acid
49
Epoxide + R-M, H2O
Epoxide opens the less substituted side
50
Alpha, beta unsaturated carbonyl + R-MgX or R-Li, H2O
1,2 Addition
51
Alpha Beta unsaturated carbonyl + R2CuLi, H2O
1,4 Addition
52
What is a good protecting group for Alcohol?
Silyl Chloride and Imidazole
53
How do you take off the protecting group for alcohol?
TBAF
54
Ketone + NaCN, HCl
H and CN add across the carbonyl bond. RCOHRCN
55
Aldehyde + NaCN, HCl
H and CN add across the carbonyl bond.
56
Ketone + Wittig Reagent
Alkene (substituted according to how substituted the starting materials were)
57
Aldehyde + Wittig Reagent
Alkene (substituted according to how the starting materials were substituted.)
58
NaBH4 will only add a nucleophilic hydride to a carbonyl carbon. True or False?
True
59
1 equivalent of H2 and Pd/C will add hydrogen across an Alkene but not a carbonyl. True or False?
True
60
2 equivalents or more of H2, Pd/C will reduce both the carbonyl bond and the Alkene. True or False?
True and it will make a secondary alcohol.
61
What type of reaction does NADH do?
It donates a nucleophilic hydride to the carbonyl carbon and then the alkoxide oxygen grabs a proton from water.
62
Internal or External Alkyne + 1. BH3 2. H2O2, -OH
Aldehyde or Ketone depending upon starting material
63
External Alkyne + 1. H2O, 2. H2SO4, HgSO4
Ketone
64
You see a carbonyl and a strong acid...what is going to happen first?
The carbonyl oxygen is going to be protonated. Acid-Base Chemistry.
65
Aldehyde or Ketone + RNH2 and mild acid
Imine (C=N-R)
66
Aldehyde or Ketone + R2NH and mild acid
Enamine (C=C-NR2)
67
Aldehyde or Ketone + H2O and Acidic/Basic
Gem-Diol
68
Aldehyde or Ketone + 2 equivalents of ROH and Acidic work up
Acetal + H2O
69
Pka strong acid (H2SO4, HCl, HBr, HI, HNO3
-9

Organic chemistry (6 decks)

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