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Organolithium reagent: Quiz


Question 1: In solution, methyllithium in THF at 1M is a tetramer, n-butyllithium in ________ at 3M is a hexamer and in THF at 1M a tetramer.

Question 2: In the solid state of methyllithium, 4 lithium atoms form a tetrahedron with each face capped by a methyl group which bonds simultaneously to three Li atoms (η3 ________).
HapticityHyperconjugationChemical bondAromaticity

Question 3: Organolithium compounds can deprotonate almost all hydrogen-containing compounds (the metalation or Li/H exchange reaction), with the exception of ________.

Question 4: A second method is the reaction of an alkyl halide or aryl alkyl sulfide with a radical ________ lithium salt, such as lithium naphthalide.
Lithium-ion batteryElectrolyteHalf cellIon

Question 5: They are therefore highly reactive nucleophiles and react with almost all types of ________.

Question 6: This is again an ________, where the most electropositive metal (lithium) will end up attached to the most electronegative organic group.
Chemical equilibriumEquilibrium constantAcid dissociation constantSolubility equilibrium

Question 7: ________, organosilicon, organoboron, organophosphorus, and organosulfur compounds are also frequently prepared by reaction of RLi with appropriate electrophiles.
Organocopper compoundOrganochlorideOrganotinOrganoboron chemistry

Question 8: Due to this reactivity they are incompatible with water, oxygen (O2), and carbon dioxide, and must be handled under a protective atmosphere such as nitrogen or, preferably, ________.

Question 9: A recent review of process chemistry indicates that the following are the most commonly used organolithium reagents: butyllithium, hexyllithium, sec-butyllithium, and ________.
Organocopper compoundOrganoboron chemistryOrganolithium reagentOrganopalladium

Question 10: Especially important in synthetic organic chemistry is the formation of ________ reagents (including Gilman reagents) by reaction of RLi with CuI or CuBr, and the preparation of organozinc reagents by reaction with ZnCl2.
Organocadmium compoundOrganoselenium chemistryOrganolithium reagentOrganocopper compound


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