General Reagents Chapter 17

Question 1

KMnO4

Answer 1

Oxidation. (to Carboxylic acid or anion)
Cyclic Alkanes -> Carboxylic acids Ph-R -> Ph-C(=O)-O
(Will replace the most acid H or the group on the benzene ring)

Aldehyde (C=O)-H -> Carboxylic Acid Anion (C=O)-O-
(Could then be protonated)

Alcohol (C-OH) -> Carboxylic Acid (C=O)
(Only works with primary alcohols)

Question 2

Ag2O

Answer 2

Oxidation. (to Carboxylic acid anion)

Aldehyde (C=O)-H -> Carboxylic Acid Anion (C=O)-O-

Question 3

Ag(NH3)2+

Answer 3

Oxidation. (to Carboxylic acid anion)

Aldehyde (C=O)-H -> Carboxylic Acid Anion (C=O)-O-

Question 4

CrO3

Answer 4

Oxidation. (to Carboxylic acid)
Aldehyde (C=O)-H -> Carboxylic Acids (C=O)-OH

Alcohol (C-OH) -> Carboxylic Acids (C=O)-OH

Question 5

H2CrO4

Answer 5

Same as CrO3. Oxidation to Carboxylic Acid

Question 6

K2Cr2O7

Answer 6

Same as CrO3. Oxidation to Carboxylic Acid

Question 7

ROH

Answer 7

Fisher Esterification or Transesterification.
(Hydrogen of the Alcohol protonates the Oxygen or Chloride and creates a leaving group, the OR of the Alcohol replaces the leaving group)

Question 8

R2NH

Answer 8

Aminolysis.
(Hydrogen of the Amine protonates the Oxygen or Chloride and creates a leaving group, the NR2 of the Amine replaces the leaving group)

Question 9

RMgX

Answer 9

Grignard.

Amides with N-H have their hydrogen removed and become anions

CO2 becomes Carboxylic Acid (C=O)-OH

Carboxylic Acids (C=O)-OH become Carboxylic Acid Anions (C=O)-O-

Acid Chlorides (C=O)-Cl, Anhydrides(C=O)-O-(C=O), and Esters (C=O)-O-R become 3* Alcohols

Question 10

RLi

Answer 10

Grignard.

Amides with N-H have their hydrogen removed and become anions

CO2 becomes Carboxylic Acid (C=O)-OH

Carboxylic Acids (C=O)-OH become Carboxylic Acid Anions (C=O)-O-

Acid Chlorides (C=O)-Cl, Anhydrides(C=O)-O-(C=O), and Esters (C=O)-O-R become 3* Alcohols (R-)(R-)C(-OH)-R

Question 11

LiAlH4

Answer 11

Reduction.

Carboxylic Acids (C=O)-OH, Acid Chlorides (C=O)-Cl, Anhydrides (C=O)-O-(C=O), and Esters (C=O)-O-R become 1* Alcohols (R-C-OH)

Amides (C=O)-NR2 become Amines H-(H-)C-NR2
(=O is replaced with -H,-H)

Question 12

LiAl(OBu)3H

Answer 12

Bulky Reduction Agent. Removes the CL of an Acid chloride, the -O-R of an Ester, or the NR2 of an Amide, changing the molecule to an Aldehyde

Question 13

H2O

Answer 13

Reactions with Carboxylic Acid creates an anion.

Reactions with Acid Chloride (C=O)-Cl, Anhydride( C=O)-O-(C=O), Ester(C=O)-O-R, or Amide (C=O)-NR2 creates a Carboxylic Acid (C=O)-OH

Question 14

H3O+

Answer 14

Turns Amides (C=O)-NR2 into Carboxylic acids (C=O)-OH

Question 15

OH-

Answer 15

Saponification (Creation of a Carboxylic Acid Anion)

Carboxylic Acids (C=O)-OH, Acid Chlorides (C=O)-Cl, Anhydrides (C=O)-O-(C=O), Esters (C=O)-O-R, and Amides (C=O)-NR2 become Carboxylic Acid Anions (C=O)-O-

Question 16

Carboxylic acid or its anion

+ Acid Chloride), (+ Heat

Answer 16

+ Acid Chloride → Anhydride

+ Heat → break away from larger compound

Question 17

Acid Chloride + Pyridine (or other base)

Answer 17

The chlorine of the acid chloride is removed and that carbon bonds with the Oxygen of the other substrate, creating an ester or anhydride.

+ Carboxylic Acids (C=O)-OH -> Anhydrides (C=O)-O-(C=O)

+ Acid Chlorides (C=O)-Cl -> Esters (C=O)-O-R

Question 18

SOCl2 or (COCl)2 or PCl5 or PCl3

Answer 18

Replaces the -OH of a Carboxylic Acid with Chloride, creating an Acid Chloride

Question 19

Benzene and AlCl3

Answer 19

Friedel Crafts Acylation. Used with the addition of an acid chloride to make a ketone

The Cl of the acid chloride is removed and the resulting molecule bonds onto the substrate