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Organic Chemistry > Addition reactions of alkenes > Flashcards

Addition reactions of alkenes Flashcards

1
Q

Addition reactions

A

Reactions with alkenes where the double bond is broken & forms 2 new sigma bonds (Addition of 2 groups)

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2
Q

Addition reactions are the reverse reactions of an ____________ reaction

A

Elimination reaction

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3
Q

Addition reaction is favored at ____________

A

Low Temp.

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4
Q

Elimination reaction are favored at ___________

A

High temp

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5
Q

Are addition reaction usually exothermic or endothermic?

A

Exothermic

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6
Q

Hydrohalogenation

A

An addition reaction that involves hydrogen & a halogen (HX, X= cl, br, or I)

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7
Q

In a hydrohalogenation reaction the H is placed on a position that already has alot of hydrogens & the halogen is placed on the more ______________

A

Substituted position

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8
Q

Markovnikov addition

A

When the H is placed on a position that has alot of hydrogens & when the halogen is placed on the more substituted position

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9
Q

Anti-Markovnikov reaction

A

The halogen is placed on the less substituted position & the H is placed on the side that doesnt have much hydrogens

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10
Q

When _______ reagents are used then the reaction will occur as markovnikov addition

A

Pure

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11
Q

When _______ reagent are used such as peroxides (ROOR) then it will occur as an anti- Markovnikov addition

A

Impure

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12
Q

What is the mechanism for hydrohalogenation?

A
  1. Proton Transfer
  2. Nucleophilic Attack
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13
Q

The regioselectivity for hydrohalogenation is what?

A

Markovnikov Addition

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14
Q

Hydrohalogenation products will have __________ centers where a pair of enantiomers will be observed

A

Chirality Center

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15
Q

Hydration

A

Addition of water (H & OH) across a double bond

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16
Q

Acid- Catalyzed Hydration

A

Addition of water across a double bond in the presence of an acid

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17
Q

The regiochemsitry of an Acid Catalyzed Hydration is what?

A

Markovnikov addition

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18
Q

What is the mechanism for an Acid - Catalyzed Hydration?

A
  1. Proton Transfer
  2. Nucleophilic Attack
  3. Proton Transfer
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19
Q

In an Acid - Catalyzed Hydration how do you control the position equilibrium?

A

Can control the position of equilibrium by controlling the amount of water present (Using either concerated or dilute acid)

20
Q

What is the stereochemistry of Acid-Catalyzed Hydration?

A

The intermediate carbocation can be attack from either side so it forms a new chirality center & a racemic mixture of enantiomers

21
Q

Oxymercuration - Demercuration

A

Addition of water (H & OH) across a double

22
Q

Mercuric Acetate

23
Q

When the double bond (π bond) is protonated in an oxymercuration - demercuration reaction what happens?

A

A carbocation intermediateis formed

24
Q

When the double bond (π bond) is attacked by a mercuric cation what happens?

A

An Mercurinium ion is formed

25
The regiochemistry of an oxymercuration-demecuration is what?
A Markonvikov addition
26
Demercuration
Removal of mercury occurs by a radial reaction & results in the addition of H & a nucleophile (which is usually water (H2O)
27
Hydroboration - Oxidation
Places the OH group on the less substituted position
28
What is the regiochemistry of an Hydroboration - Oxidation Reaction?
Anti- Markovnikov addition
29
What is the stereochemistry of a Hydroboration - oxidation reaction ?
Syn Addition (The prodcuts chirality centers have the H & OH on the same plane (Cis conformation))
30
If there is no chirality center formed in an hydroboration-oxidation reaction then what are the outcome of the products?
There will only be one product formed
31
When only one chirality center present in the products of an hydroboration - oxidation reaction then what is the outcome of the products?
Both enantiomers are observed
32
When there is two chirality center present in the products of an hydroboration reaction then what is the outcome of the products?
The chirality center are formed by a syn addition (So they are on the same plane) & a pair of enantiomer is observed
33
Catalytic Hydrogenation
Involves the addition of molecular hydrogen (H2) across a double in the presence of a metal catalyst
34
What is the stereochemistry of catalytic hydrogenation ?
When two new chirality center are formed then a pair of enantiomers are formed by a syn addition
35
What are the common heterogenous Catalyst in a catalytic hydrogenation reaction?
Pt, Pd, & Ni (They dont dissolve in a reaction)
36
What is the common homogeneous catalyst in a catalytic hydrogenation?
Wilkinson's Catalyst (Rh(PPh3)3Cl)
37
Halogenation
Involves the addition of X2 (Either Br2 or Cl2) across an alkene
38
What is the regiochemistry of halogenation reaction?
Anti-Markonvikov addition
39
What is the stereochemistry of an halogenation reaction?
Anti Addition where the products will have the halogens on the opposite planes
40
In an Halohydrin reaction the OH is placed on what?
the more substituted position
41
What is the indications of a halohydrin reaction?
When you have a halogenation (either Br2 or Cl2) as a reagent & water as the solvent (Adds a halogen & OH across a double bond & the OH is placed on the more substituted position )
42
Dihydroxylation
Adding two OH
43
Halohyrin can make an epoxide through an ________ reaction
SN2
44
Ozonolysis Reaction
A reaction that cleaves the double bond ( The common reagents are DMS & ZN/H2O)
45
What do have consider when predicting the products of an addition reaction?
1. What groups are being added across a double bond 2. What is the expected regiochemistry (markovnikov addition or anti- markovnikov addition) 3. What is the expected stereochemistry (Syn or Anti addition)
46
How do you change the position of a leaving group?
1. Elimination reaction 2. Addition reaction
47
How do you change the position of a double bond (π bond)?
1. Addition reaction 2 Elimination reaction

Organic Chemistry (47 decks)

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