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Organic Chemistry > Reactions > Flashcards

Reactions Flashcards

1
Q

Which step is slow for Electrophilic Additions?

A

First step

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2
Q

What does the first step of electrophilic additions form?

A

Carbocations

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3
Q

Another term for Nucelophile

A

Lewis Base

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4
Q

Another term for Electrophile

A

Lewis Acid

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5
Q

Lewis Base

A

Gives up an electron pair

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6
Q

Lewis Acid

A

Accepts electron pair

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7
Q

What should you always look for for electrophilic additions?

A

Rearrangement of carbocation

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8
Q

Types of rearrengement

A

Hydride shift, methyl shift, and ring expansion.

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9
Q

Markovnikov’s Rule

A

Nucleophile attached to most substituted carbon.

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10
Q

First 5 Electrophilic Additions

A
  1. Addition of a Hydrogen Halide (HX)
  2. Antimarkovnikov HBR
  3. Acid Catalyzed Hydration
  4. Addition of a Br2 or Cl2
  5. Formation of a Hydrogenated Alcohol (halohydrin)
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11
Q

Addition of a Hydrogen Halide (HX) properties

A

Markovnikov, Br = regioselective, HBr faster than HCl, possibility of polar solvent

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12
Q

Peroxide presence indicates what?

A

Free radical mechanism

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13
Q

What does the most substituted carbon mean?

A

Carbon with the least amount of hydrogens.

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14
Q

Properties of Antimarkovnikov HBr

A

Free radical mechanism, Antimarkovnikov, only HBr, presence of peroxide leads to antimarkovnikov.

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15
Q

Acid Catalyzed Hydration required reagents

A

Nu: H2O and E: H+ (acid)

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16
Q

Acid Catalyzed Hydration Properties

A

Markovnikov and look for rearrangement.

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17
Q

Stereospecificity

A

Stereochemistry of reactants determines stereochemistry of products. Hence look at Stereochemistry

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18
Q

Solvents for addition of Br2 or Cl2

A

CCl4 or CH2Cl2 inert solvent

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19
Q

Properties of Addition of Br2 or Cl2

A

Antiaddition (use of bridge), stereospecificity for cycloalkenes (look at stereochemistry).

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20
Q

Halohydrin

A

Halogenated Alcohol

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21
Q

Formation of a halogenated alcohol (halohydrin) properties

A

Antiaddition (use of bridge), OH attaches to most substituted carbon (due to charge stability), and look at stereochemistry.

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22
Q

Last 5 electrophilic addition reactions

A
  1. Addition of Sulfuric Acid - like hell - remember 6
  2. Hydroboration/Oxidation
  3. Formation of a Diol (glycol)
  4. Formation of Aldehydes + Ketones
  5. Hydrogenation
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23
Q

Formation of a halogenated alcohol required solvent

A

excess H2O

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24
Q

Sulfuric Acid formula

A

H2SO4

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25
Q

Addition of Sulfuric Acid solvent requirements

A

dilute H2O and heat

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26
Q

Addition of Sulfuric Acid properties

A

Markovnikov

27
Q

Solvents for Hydroboration/Oxidation

A
  1. BH3

2. H2O2, NaOH (oxidation)

28
Q

BR3

A

Triakyl Borane

29
Q

Intermediary product of addition of sulfuric acid

A

Sulfinated Alkane

30
Q

2 electrophilic additions that are antimarkovnikov

A

Antimarkovnikov HBR and Hydroboration/Oxidation

31
Q

Properties of Hydroboration/Oxidation

A

Antimarkovnikov - OH attaches to least substituted.

Syn Addition - OH and H attached on same side.

32
Q

Glycol

A

diol - 2OH

33
Q

3 electrophilic additions that involve oxidation

A
  1. Hydroboration/Oxidation
  2. Formation of diol (glycol)
  3. Formation of Aldehydes + Ketones
34
Q

Required reagents for Formation of diol (glycol)

A
  1. OsO4

2. Na2SO3, H2O (oxidation)

35
Q

OsO4

A

Osmium Tetroxide.

36
Q

Properties of formation of diol

A

Syn addition and stereochemistry.

37
Q

Type of oxidation involved in formation of diol

A

Oxidation without cleavage.

38
Q

2 sub reactions in formation of Aldehydes + ketones

A

Ozonolysis and Hot KMnO4

39
Q

Oxidation type involved in formation of aldehydes + ketones.

A

Oxidation with cleavage

40
Q

Ozone

41
Q

Ozonolysis Reagents

A

O3 and CH3-S-CH3

42
Q

Hot KMnO4 reagents

A

KMnO4, H2O, OH-

43
Q

KMnO4 unsubstituted carbon

44
Q

KMnO4 monosubstituted carbon

A

Carboxylic Acid

45
Q

KMnO4 disubstituted carbon

A

ketones + aldehydes

46
Q

Property of Hydrogenation

A

Syn reduction

47
Q

Normal Hydrogenation Reagents

A

Pt, Ni, Heat and H2

48
Q

Lindlar Catalyst alternative

A

Ni2B (P-2)

49
Q

Lindlar Catalyst resulting product

50
Q

Dissolving Metal Reduction required reagents

A

H2 and Li or Na Metal, EtNH2 or NH4Cl

51
Q

Dissolving Metal Reduction results in

52
Q

How many moles of strong base do you need to synthesize internal alkyne?

53
Q

How many moles of strong base do you need to synthesize terminal alkyne?

54
Q

Synthesis of Alkynes Requirements

A

Strong Base, Anticoplanar hydrogen

55
Q

Alkylation

A

Extending Carbon Chain

56
Q

Requirements for Alkylation

A

Strong Base

57
Q

NaH

A

Sodium Hydride, strong base.

58
Q

Strong bases for alkylation

A

NaH
NaNH2 / NH3(l)
LDA - Li diisopropylamide

59
Q

Link between substitution and stability

A

Most substituted double bond is most stable

60
Q

Trans double bonds vs cis double bonds (which one is more stable?)

A

Trans double bonds.

61
Q

Zaitsev’s rule

A

Product with most substituted double bond favored

62
Q

Hoffman Product

A

Bulky Base, double bond is least substituted (major)

63
Q

Electrophilic Additions, which atom does the double bond add first?

A

The less electronegative one

Organic Chemistry (4 decks)

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