Reactions of Ethers, Epoxides, Aldehydes, and Ketones

Question 1

Acidic cleavage of an ether

Answer 1

HBr

Question 2

Based-catalyzed epoxide ring opening

Answer 2

1) Negative or neutral nucleophile / 2) H3O+ [Possible nucleophiles: RO-, RS-, RMgX, RLi, LAH, R2N-]

Question 3

Thioacetal formation

Answer 3

2RSH, cat. HCl

Question 4

Hydrate formation

Answer 4

H2O, cat. H2SO4

Question 5

Epoxide synthesis from halohydrin

Answer 5

NaH

Question 6

Enamine formation

Answer 6

R2NH, [H2SO4]

Question 7

Linear acetal formation

Answer 7

2ROH, cat. H2SO4

Question 8

Baeyer-Villiger reaction (ester formation)

Answer 8

RCO3H

Question 9

Williamson Ether Synthesis (asymmetrical ether synthesis)

Answer 9

X-R, NaH

Question 10

Ether synthesis by markovnikov addition (no rearrangement)

Answer 10

1) Hg(OAc)2, ROH / 2) NaBH4

Question 11

Cyanohydrin formation

Answer 11

KCN, cat. HCl

Question 12

Cyclic acetal formation

Answer 12

HO-C-C-OH, cat. H2SO4

Question 13

Ether synthesis by markovnikov addition (rearrangement)

Answer 13

ROH / H2SO4

Question 14

Epoxide synthesis from alkene

Answer 14

mCPBA or RCO3H

Question 15

Imine formation

Answer 15

RNH2, [H2SO4]

Question 16

Acetal removal

Answer 16

cat. H2SO4

Question 17

Wittig reaction (alkyl halide and carbonyl to alkene)

Answer 17

1) PPh3, 2) n-BuLi / 3) aldehyde or ketone

Question 18

Acid-catalyzed epoxide ring opening

Answer 18

Nucleophile / Catalytic acid

Question 19

Thioacetal reduction (to alkane)

Answer 19

Raney Ni / H2

Question 20

Hydrazone (C=N-NHR) formation

Answer 20

H2N-NHR / cat. HCl

Question 21

Oxime (C=N-OH) formation

Answer 21

HONH2 / cat. HCl

Question 22

Dehydration (symmetrical ether synthesis)

Answer 22

H2SO4 / heat