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Organic Chemistry > CH325 exam 1 > Flashcards

CH325 exam 1 Flashcards

(70 cards)

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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
addition of halogen in an invert solvent reactants:
alkene and X2
26
addition of halogen in an invert solvent products:
X-C-C-X (anti addition)
27
halohydrin formation reactants:
alkene and H20 and X2
28
halohydrin formation product:
X-C-C-OH
29
where does the halogen attach in halohydrin formation?
to the C with more H atoms
30
oxymercuration reduction reactants:
alkene and Hg(OAc)2 and H20 and NaBH4 and NaOH [2 step rxn]
31
oxymercuration reduction products:
H-C-C-OH
32
oxymercuration reduction intermediate:
meconium ion cyclopropane with Hg-OAc as one of the corners
33
epoxidation reactants:
alkene and peroxy acid
34
what is peroxy acid?
R-COOH
35
epoxidation product:
cyclopropane with O in one corner
36
alkene hydroboration oxidation reactants:
37
alkene hydroboration oxidation product:
38
catalytic hydrogenation reactants:
alkene and H+ and Pt (or Pd)
39
catalytic hydrogenation product:
H-C-C-H
40
Addition to conjugated dienes reactants:
C=C-C=C and HX
41
addition to conjugated dienes product:
CH-C(X)-C=C CH-C=C-C(X)
42
what is the product of a conjugated diene reaction at high temp?
1,4 addition
43
addition of hydrogen halides to alkynes reactants:
alkyne and HX
44
addition of hydrogen halides to alkynes product:
X-C=CH2
45
addition of water to alkyne reactants:
alkyne and H2O and H+
46
addition of water to alkyne products:
C-C(OH)=CH2
47
alkyne oxymercuration reduction reactants:
alkyne and Hg 2+ and H2O and H2SO4
48
alkyne oxymercuration reduction product:
C-C(OH)=CH2
49
alkyne hydroboration oxidation reactants:
internal alkyne: BH3, THF, H2O, NaOH terminal alkyne: R2BH, H2O, NaOH
50
alkyne hydroboration oxidation products:
internal alkyne: ketone terminal alkyne: aldehyde
51
addition of Br2 to alkynes reactants:
alkyne and Br2
52
addition of Br2 to alkynes products:
Br-C=C-Br
53
catalytic hydrogenation reactants:
alkyne + - Pd, H2 - Lindler, H2 - Na or Li, NH3
54
catalytic hydrogenation product for Pd,H2:
C-C (both have two H atom on them)
55
catalytic hydrogenation product for Lindlar, H2:
alkane with syn addition
56
catalytic hydrogenation product for Na/Li, NH3:
alkane with anti addition
57
what is the stereochemistry of an SN2 reaction?
Nu back attack, remaining three groups 'flip' to other side
58
What happens to the strength of a Nu when the size of them molecule increases?
strength increase
59
What happens to the strength of the Nu when the electronegativity increases?
strength decreases
60
What is true of the strength of a negatively charged Nu?
increased strength
61
What happens to Nu strength when the steric bulk decreases?
increased strength
62
What type of reaction doesn't have good Nu present?
SN1
63
What is the mechanism of reaction for an SN1 reaction?
bond breaking between electrophilic C and the LG is complete before bond with Nu is formed
64
what is the first step in an SN1 reaction?
ionize the C-X bond to get carbocation intermediate
65
What is step two of an SN2 reaction?
react carbocation with Nu to get product
66
What type of solvents are involved in an SN2 reaction?
polar aprotic
67
What type of solvents are involved in an SN1 reaction?
polar protic
68
What are the steps to determine SN1 vs SN2 reactions?
1. structure of substrate 2. strength of Nu 3. solvent used in that order ^^
69
Structure of substrates:
SN1: 3º > 2º > 1º > CH3 SN2: CH3 > 1º > 2º > 3º
70
What is the stereochemistry of SN2?
inverse

Organic Chemistry (4 decks)

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