Chapter 19: Carbonyls Flashcards
1
Q
Oxidizing reagents of secondary alcohols
A
- also turns primary alcohols and aldehydes into carboxylic acids
2
Q
Oxidizing reagents of primary alcohols
A
3
Q
Ozonolysis
A
- essentially takes every C=C bond in a compund and breaks it apart into two C=O bonds
4
Q
Reactivity of Carbonyls
A
- A carbonyl group can be attacked by a nucleophile
- After a carbonyl is attacked, it will try to reform if possible
5
Q
H-nucleophiles
A
- source of negatively charged hydrogens (hydride ions)
6
Q
A
7
Q
O-nucleophiles
A
- turn aldehydes into acetals (ketones to ketals), going through a hemiacetal intermediate
8
Q
A
9
Q
A
10
Q
Protecting ketones
A
-ketones can be protected from reducing agents by turning it into an acetal
11
Q
Clemmenson Reduction
A
- useful in acidic conditions
12
Q
S-nucleophiles
A
- very similiar to O-nucleophiles, except BF3 used to make carbonyl more electrophilic, forms thioacetals
13
Q
thioacetals can be reduced
A
14
Q
3 types of reduction?
A
- Clemmenson = acidic conditions
- Raney Ni = nuetral conditions
- Hydrazone = basic conditions
15
Q
Ketones + Primary amines
A
makes imines
16
Q
Ketone + Secondary amine
A
makes enamines
17
Q
Alcohols, primary amines, and secondary amines all react with ketones following this mechanism
A
18
Q
Oximes
A
19
Q
Hydrozones
A
20
Q
Reduction of hydrozones
A
21
Q
Synthesis of alkanes from ketones
“Wolf-Kirchner Reduction”
A
22
Q
Forming grignard reagents
A
- carbon does not hold - charge very well = very reactive
- can’t perform these reactions in any kind of acid, even water
- or any compound with acidic protons
23
Q
Carbonyls and grignards
A
24
Q
Ylides
A
- compound with 2 adjacent, oppositely charged atoms
- functions as a carbon nucleophile
25
Q
Formation of ylides from TPP
A
26
Q
Wittig reaction
A
27
Q
Sulfur Ylides
A
- formed the same as phosphorus ylides, but start with DMS
- very different products from Phosphorous ylides though, form epoxides not alkenes
28
Q
A
29
Q
Cyanohydrin Formation
A
30
Q
Catalytic Hydrogenation
A
