RXNs

Question 1

Primary alcohol

Answer 1

1. Reduction w/ NaBH4 of aldehyde
2. Aldehyde w/ OM reagent(organolithlium)
3. Ester w/(1.LAH,2.H3O+) @RT
4. Carboxylic acid (1.LAH,2.H3O+) @Low Temp - RT

Question 2

Secondary alcohol

Answer 2

1. Reduction (LiAlH6, THF 2.H2O) of ketone

2. OM w/ aldehyde

Question 3

Tertiary alcohol

Answer 3

1. Ketone w/ OM reagent(1.OM,THF-2.H2O)

2. Ester + 1. Grignard, 2. H2O

Question 4

Carboxylic Acids

Answer 4

1. Carbonation of grignard
2. Oxidation of primary alcohol (Chromic acid oxidation w/ JONES reagent)
3. Acid-Catalyzed Hydrolysis of Ester (Ester + H2O) P-N-D-P LG- D
4. Base-Promoted Hydrolysis of Ester (Ester + NaOH) N-LG-D-P
5. Carboxylic acid derivative hydrolysis
   Acid chloride, Acid anhydride, Ester(3,4), Amide, Nitrile

Question 5

Aldehyde

Answer 5

1. PCC or PDC oxidation of primary alcohol w/ PCC or PDC and MeCl2
2. Amide + (1.LAH,2.H2O) 0C

Question 6

Ketone

Answer 6

1. PCC or PDC oxidation of secondary alcohol w/ PCC or PDC and CH2Cl2
2. Oxidation of secondary alcohol (Chromic acid oxidation w/ JONES reagent)
3. Amide + Grignard (1.Grig - 2.H3O+)

Question 7

Esters

Answer 7

1. Acid-Cat’d Esterification from Carboxylic acid + ROH
   (Protination - Nuc attack - Deprotination - Protination + H2O LG - Deprotination)
2. O Acylation - Acid Chloride + ROH (pyridine)
3. 2. O Acylation - Acid Anhydride + ROH (pyridine)

Question 8

Amide

Answer 8

1. N acylation W/ Acid Chloride + 2 Me2NH
2. N acylation W/ Acid Anhydride + 2 Me2NH
3. Aminolysis W/ Ester + NH3 + Heat

Question 9

Preparation of acid chloride

Answer 9

1. Carboxylic acid + PCl5 or PCl3

2. Carboxylic acid + Thionyl Chloride

Question 10

Preparation of Anhydrides

Answer 10

1. Acid chloride and carboxylate

Question 11

Amine

Answer 11

1. Amide + 1.LAH, 2. H2O (@RT)

2. . Nitrile + (1.LAH,Et2O, 2.H2O) –> 1o Amine