SLE214 tutorial 7 Solutions

Q1. Describe the conditions necessary for the formation of Grignard reagents. Why does the solvent have to be free of water? What roles can Grignard reagents perform? Would ethanol be a good solvent for a Grignard reagent? Why/Why not? RX + Mg (s) R-Mg-X Normally performed in dry ether or THF. Solvent must be free of water otherwise once Grignard has formed it will function as a base and take a proton from water to form an alkane and hydroxide. Grignard reagents can be nucleophiles or bases. Ethanol is no good as the O-H will be deprotonated to form an alkane and an alkoxide anion. Q2. Provide the products and the mechanisms for the following reactions.

a.

NaCN = Na and :CN:

OH TsCl

pyridine

OTs

NaCN

SN2 reaction

CN

N = pyridine (base - possibly deprotonates ROH prior to reaction) S O TsCl

keeps reaction conditions basic - otherwise HCl buidup will stop reaction

b.

Cl

c.

d.

Q3. Identify the reagents (suggest solvents if you like) a and b required to effect the following transformations. What type of reaction is the final step. What combination of reagents would have provided the final product directly from the alcohol?
solvent THF or Et2O i. LiAlH 4 O ii. H+ E2 elimination OH SOCl2 neat H LiAlH 4 = H O O H+ Cl
EtMgBr

OH

Could form alkene directly from alcohol using POCl3 and pyridine Q4. What reagents would you use to effect the following transformations?
SN2 NaCN polar aorotic l t
Red'n i. LiAlH4 or C N NaBH4

NH2

ii H 2O