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1. What is the major product when (CH3)2CHCH2CH2Br is subjected to the following

ID: 1013417 • Letter: 1

Question

1. What is the major product when (CH3)2CHCH2CH2Br is subjected to the following reaction sequence: 1. Mg, ether 2. CO2 3. H3O+?

A) 3-methyl-1-butanol

B) 4-methylpentanoic acid

C) 4-methyl-1-pentanol

D) 2-methyl-2-butanol

3. Which of the following reagents cannot be used in the synthesis of a Gilman reagent? Select all that Apply.

A. Lithium metal B. Lithium halide C. alkyl halide D. aryl halide E. CuBr

4. Which catalysts are common in the Stille coupling?

A) Pd(PPh3)4

B) Pd (OAc)2

C) PdCl2(PPh3)2

D) All of the above

E) None of the above

Explanation / Answer

1.B) 4-methylpentanoic acid

Grignard reagent (CH3)2CHCH2CH2MgBr ) ----> (CH3)2CHCH2CH2CO2- --> (CH3)2CHCH2CH2CO2H protonation

2.  C. alkyl halide D. aryl halide

3. A) Pd(PPh3)4