Chapter 22: 19P (page 868)
Which of the following species represent organometallic compounds:
(a)BrMgCCCH2CH3 ; (b) NaOCH2CH3 ; (c)KOC(CH3)3 ; (d) PhLi?
Short Answer
Answer
(a)BrMgC CCH2CH3 and (d)PhLi represent an organometallic compound.
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Chapter 22: 19P (page 868)
Which of the following species represent organometallic compounds:
(a)BrMgCCCH2CH3 ; (b) NaOCH2CH3 ; (c)KOC(CH3)3 ; (d) PhLi?
Answer
(a)BrMgC CCH2CH3 and (d)PhLi represent an organometallic compound.
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What epoxide is needed to convertCH3CH2MgBrto each of the following alcohols, after quenching with water?
a.

b.

c.

d.

Question: Rank the compounds in each group in order of increasing reactivity in nucleophilic acyl substitution.
Question: Devise a synthesis of each compound from benzene and organic alcohols containing four or fewer carbons. You may also use any required organic or inorganic reagents.
a. 
b. 
Draw the product formed when pentanal (CH3CH2CH2CH2CHO ) is treated with each reagent. With some reagents, no reaction occurs.
a. NaBH4 , CH3OH
b. {1} LiAlH4 ; {2} H2O
c. H2,Pd-C
d. PCC
e. Na2Cr2O7, H2SO4, H2O
f. Ag2O, NH4OH
g. {1}CH3MgBr ; {2} H2O
h. {1} C6H5Li ; {2} H2O
i. {1} (CH3)2CuLi ; {2} H2O
l. The product in (a) , then TBDMS-Cl , imidazole
What product is formed when each compound is treated with either LiAlH4 (followed by H2O ), or NaBH4 in CH3OH ?
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