Reactions

Question 1

Which step is slow for Electrophilic Additions?

Answer 1

First step

Question 2

What does the first step of electrophilic additions form?

Answer 2

Carbocations

Question 3

Another term for Nucelophile

Answer 3

Lewis Base

Question 4

Another term for Electrophile

Answer 4

Lewis Acid

Question 5

Lewis Base

Answer 5

Gives up an electron pair

Question 6

Lewis Acid

Answer 6

Accepts electron pair

Question 7

What should you always look for for electrophilic additions?

Answer 7

Rearrangement of carbocation

Question 8

Types of rearrengement

Answer 8

Hydride shift, methyl shift, and ring expansion.

Question 9

Markovnikov’s Rule

Answer 9

Nucleophile attached to most substituted carbon.

Question 10

First 5 Electrophilic Additions

Answer 10

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)

Question 11

Addition of a Hydrogen Halide (HX) properties

Answer 11

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

Question 12

Peroxide presence indicates what?

Answer 12

Free radical mechanism

Question 13

What does the most substituted carbon mean?

Answer 13

Carbon with the least amount of hydrogens.

Question 14

Properties of Antimarkovnikov HBr

Answer 14

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

Question 15

Acid Catalyzed Hydration required reagents

Answer 15

Nu: H2O and E: H+ (acid)

Question 16

Acid Catalyzed Hydration Properties

Answer 16

Markovnikov and look for rearrangement.

Question 17

Stereospecificity

Answer 17

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

Question 18

Solvents for addition of Br2 or Cl2

Answer 18

CCl4 or CH2Cl2 inert solvent

Question 19

Properties of Addition of Br2 or Cl2

Answer 19

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

Question 20

Halohydrin

Answer 20

Halogenated Alcohol

Question 21

Formation of a halogenated alcohol (halohydrin) properties

Answer 21

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

Question 22

Last 5 electrophilic addition reactions

Answer 22

6. Addition of Sulfuric Acid - like hell - remember 6
7. Hydroboration/Oxidation
8. Formation of a Diol (glycol)
9. Formation of Aldehydes + Ketones
10. Hydrogenation

Question 23

Formation of a halogenated alcohol required solvent

Answer 23

excess H2O

Question 24

Sulfuric Acid formula

Answer 24

H2SO4

Question 25

Addition of Sulfuric Acid solvent requirements

Answer 25

dilute H2O and heat

Question 26

Addition of Sulfuric Acid properties

Answer 26

Markovnikov

Question 27

Solvents for Hydroboration/Oxidation

Answer 27

1. BH3 | 2. H2O2, NaOH (oxidation)

Question 28

BR3

Answer 28

Triakyl Borane

Question 29

Intermediary product of addition of sulfuric acid

Answer 29

Sulfinated Alkane

Question 30

2 electrophilic additions that are antimarkovnikov

Answer 30

Antimarkovnikov HBR and Hydroboration/Oxidation

Question 31

Properties of Hydroboration/Oxidation

Answer 31

Antimarkovnikov - OH attaches to least substituted. | Syn Addition - OH and H attached on same side.

Question 32

Glycol

Answer 32

diol - 2OH

Question 33

3 electrophilic additions that involve oxidation

Answer 33

7. Hydroboration/Oxidation 8. Formation of diol (glycol) 9. Formation of Aldehydes + Ketones

Question 34

Required reagents for Formation of diol (glycol)

Answer 34

1. OsO4 | 2. Na2SO3, H2O (oxidation)

Question 35

OsO4

Answer 35

Osmium Tetroxide.

Question 36

Properties of formation of diol

Answer 36

Syn addition and stereochemistry.

Question 37

Type of oxidation involved in formation of diol

Answer 37

Oxidation without cleavage.

Question 38

2 sub reactions in formation of Aldehydes + ketones

Answer 38

Ozonolysis and Hot KMnO4

Question 39

Oxidation type involved in formation of aldehydes + ketones.

Answer 39

Oxidation with cleavage

Question 40

Ozone

Answer 40

O3

Question 41

Ozonolysis Reagents

Answer 41

O3 and CH3-S-CH3

Question 42

Hot KMnO4 reagents

Answer 42

KMnO4, H2O, OH-

Question 43

KMnO4 unsubstituted carbon

Answer 43

CO2

Question 44

KMnO4 monosubstituted carbon

Answer 44

Carboxylic Acid

Question 45

KMnO4 disubstituted carbon

Answer 45

ketones + aldehydes

Question 46

Property of Hydrogenation

Answer 46

Syn reduction

Question 47

Normal Hydrogenation Reagents

Answer 47

Pt, Ni, Heat and H2

Question 48

Lindlar Catalyst alternative

Answer 48

Ni2B (P-2)

Question 49

Lindlar Catalyst resulting product

Answer 49

Cis

Question 50

Dissolving Metal Reduction required reagents

Answer 50

H2 and Li or Na Metal, EtNH2 or NH4Cl

Question 51

Dissolving Metal Reduction results in

Answer 51

Trans

Question 52

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

Answer 52

2

Question 53

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

Answer 53

3

Question 54

Synthesis of Alkynes Requirements

Answer 54

Strong Base, Anticoplanar hydrogen

Question 55

Alkylation

Answer 55

Extending Carbon Chain

Question 56

Requirements for Alkylation

Answer 56

Strong Base

Question 57

NaH

Answer 57

Sodium Hydride, strong base.

Question 58

Strong bases for alkylation

Answer 58

NaH NaNH2 / NH3(l) LDA - Li diisopropylamide

Question 59

Link between substitution and stability

Answer 59

Most substituted double bond is most stable

Question 60

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

Answer 60

Trans double bonds.

Question 61

Zaitsev's rule

Answer 61

Product with most substituted double bond favored

Question 62

Hoffman Product

Answer 62

Bulky Base, double bond is least substituted (major)

Question 63

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

Answer 63

The less electronegative one