Question

Complete the following reactions which form ethers (A and B) and cyclic ethers (C-E) as major products. SHOW MECHANISMS FOR ALL

A) (1R, 2R)1,2-dimethylpropan-1-ol (2 has a dash Methyl and 1 has a wedge methyl) reacts with NaH/CH3CH2Br

B) 3-methylpent-3-ene reacts with Hg(OAc)2/ CH3CH2OH, NaBH4

C) 2-cyano-6-methyl cyclohept-1,4,6-triene-4-al reacts with MCPBA/CH2Cl2

D) (2R,3S)- 2-bromo-butan-3-ol reacts with NaOH

E) Cyclobutyl as the base chain with (CH2OH attached at Carbon 1 and CH2CH2Br attached at carbon 2) reacts with KOH

F) 2-methylcyclohexene reacts with 1. Hg(OAc)2 in MeOH, H^+, NaBH4

G) Phenol (with CH2OH attached to carbon 2) reacts with Na/CH3CH2Br

I) Phenol (with OH attached to carbon 2) reacts with NaOH/CH3CH2Br

J) 2-chlorocyclohexanol reacts with NaOH

K) 3-bromo-pentan-2-ol reacts with NaOH

L) 6-bromo-4-methyl-hexan-2-ol reacts with KOH

M) (3R)-4-bromo-2,3-dimethylbutan-1-ol reacts with NaOH

N) 3,4-epoxy-pentane reacts with 1. H2SO4 / 2.CH3OH

O) 3,4-epoxy-pentane reacts with 1.NaOCH2CH3 / 2.CH3OH

P) 2,3-epoxy-2-methyl-butane NaNH2 / CH3CH2OH

Q) 2,3-epoxy-2-methyl-butane reacts with 1. H2SO4 / 2.CH3SH

Answer 1