reagents for ether, epoxide and thioether mechanisms

Question 1

ether from alcohol dehydration

Answer 1

H2SO4

Question 2

williamson ether synthesis for symmetrical ethers

Answer 2

alkoxide at nucleophile and alkyl halide as electrophile

Question 3

alkoxide anion

Answer 3

• Na or K to deprotonate
• rest of the group and OTs are a good leaving group

Question 4

williamson synthesis for unsymmetrical ethers

Answer 4

alkoxide at nucleophile and alkyl halide as electrophile

Question 5

alkoxymercuration demurcuration

Answer 5

alkene is the nucleophile and Hg(OAc)2 is the electrophile

Question 6

ether cleavage

Answer 6

HBr and HI

Question 7

thioethers

Answer 7

ether but instead of oxygen, it is sulfur
- DMSO is polar aprotic solvent

Question 8

silyl ethers

Answer 8

TBDMS protecting group to deprotonate OH and F- for regenerating OH

Question 9

synthesis of epoxides syn addition

Answer 9

alkenes and per acids (MCPBA)

Question 10

synthesis of epoxides trans addition

Answer 10

MMPP and H20/CH3N

Question 11

synthesis of epoxides from halohydrins

Answer 11

base (NaOH)

Question 12

alkene conversion to halohydrins

Answer 12

X2 and H20

Question 13

acid catalyzed ring openings

Answer 13

HCl,HBr,HI, H2O, ROH in presence of acid can open rings and act as nucleophiles
- H2SO4 protonates epoxides

Question 14

unsymmetrical epoxides halohydrin

Answer 14

HCl or any halide

Question 15

base catalyzed ring openings

Answer 15

Nuc: -OH, -OR, -CN, -SR, NH3

Question 16

unsymmetrical ether base catalyzed ring opening

Answer 16

same as normal base catalyzed ring openings but it attacks less substituted carbon

Question 17

organometallic reagents

Answer 17

RLi, RMgX, and R2CuLi
and H2O protonates O-