Ch 11 Reactions

Question 1

Alcohol –> Alkyl tosylate

Answer 1

TsCl, pyridine

Question 2

Alcohol –> Alkyl mesylate

Answer 2

MsCl, pyridine

Question 3

Alcohol –> Alkane

Answer 3

1) TsCl, pyridine 2) LAH, NaBH4

Question 4

Primary or Secondary Alcohol –> Alkyl Bromide (stereochemical inversion)

Answer 4

PBr3

Question 5

Primary or Secondary Alcohol –> Alkyl chloride (stereochemical inversion)

Answer 5

PCl3

Question 6

Alcohol –> Alkyl chloride (stereochemical retention)

Answer 6

SOCl2, dioxane solvent

Question 7

Primary Alcohol –> Carboxylic Acid (chromium reagents)

Answer 7

Jones Reagent (H2CrO4 in acetone), Na2Cr2O7, CrO3 – all in ACIDIC solvent

Question 8

Primary alcohol –> Carboxylic acid (non-chromium reagents)

Answer 8

NaOCl

Question 9

Primary alcohol –> Aldehyde (non-chromium reagents)

Answer 9

Swern oxidation, Dess-Martin Periodinate

Question 10

Primary Alcohol –> Aldehyde (chromium reagents)

Answer 10

PCC: CrO3, Pyridine HCl in CH2Cl2 ANHYDROUS

Question 11

Secondary alcohol –> Ketone

Answer 11

All chromium reagents and all non-chromium reagents

Question 12

Alcohol –> carbonyl (Biological oxidation)

Answer 12

Enzyme, alcohol, and NAD+

Question 13

Alcohol –> Alkene (1)

Answer 13

Acid-catalyzed dehydration: H+/H2O and heat

Question 14

Alcohol –> Alkene (2)

Answer 14

Tosylation and t-BuO-

Question 15

Alcohol –> Alkene (3)

Answer 15

POCl3

Question 16

Diol –> Carbonyl

Answer 16

Pinacol rearrangement: Acidic conditions

Question 17

Alcohol –> Ester

Answer 17

Fisher esterification: acid catalyzed

Question 18

Alcohol –> Ester

Answer 18

Acid chloride esterification: Acid chloride and pyrimidine