Chapter 19: Carbonyls

Question 1

Oxidizing reagents of secondary alcohols

Answer 1

• also turns primary alcohols and aldehydes into carboxylic acids

Question 2

Oxidizing reagents of primary alcohols

Answer 2

Question 3

Ozonolysis

Answer 3

• essentially takes every C=C bond in a compund and breaks it apart into two C=O bonds

Question 4

Reactivity of Carbonyls

Answer 4

• A carbonyl group can be attacked by a nucleophile
• After a carbonyl is attacked, it will try to reform if possible

Question 5

H-nucleophiles

Answer 5

• source of negatively charged hydrogens (hydride ions)

Question 6

Answer 6

Question 7

O-nucleophiles

Answer 7

• turn aldehydes into acetals (ketones to ketals), going through a hemiacetal intermediate

Question 8

Answer 8

Question 9

Answer 9

Question 10

Protecting ketones

Answer 10

-ketones can be protected from reducing agents by turning it into an acetal

Question 11

Clemmenson Reduction

Answer 11

• useful in acidic conditions

Question 12

S-nucleophiles

Answer 12

• very similiar to O-nucleophiles, except BF3 used to make carbonyl more electrophilic, forms thioacetals

Question 13

thioacetals can be reduced

Answer 13

Question 14

3 types of reduction?

Answer 14

• Clemmenson = acidic conditions
• Raney Ni = nuetral conditions
• Hydrazone = basic conditions

Question 15

Ketones + Primary amines

Answer 15

makes imines

Question 16

Ketone + Secondary amine

Answer 16

makes enamines

Question 17

Alcohols, primary amines, and secondary amines all react with ketones following this mechanism

Answer 17

Question 18

Oximes

Answer 18

Question 19

Hydrozones

Answer 19

Question 20

Reduction of hydrozones

Answer 20

Question 21

Synthesis of alkanes from ketones

“Wolf-Kirchner Reduction”

Answer 21

Question 22

Forming grignard reagents

Answer 22

• 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

Question 23

Carbonyls and grignards

Answer 23

Question 24

Ylides

Answer 24

• compound with 2 adjacent, oppositely charged atoms
  
  • functions as a carbon nucleophile

Question 25

Formation of ylides from TPP

Answer 25

Question 26

Wittig reaction

Answer 26

Question 27

Sulfur Ylides

Answer 27

* formed the same as phosphorus ylides, but start with DMS * very different products from Phosphorous ylides though, form epoxides not alkenes

Question 28

Answer 28

Question 29

Cyanohydrin Formation

Answer 29

Question 30

Catalytic Hydrogenation

Answer 30