When acetone (H_3CCOCH_3) is treated with CH_3MgBr followed by addition of H_2O.

Question

When acetone (H_3CCOCH_3) is treated with CH_3MgBr followed by addition of H_2O. what general class of product results? a) 1 degree alcohol b) 2 degree alochol C) 3 degree alcohol d) none of these 14. Which of the following alcohols will not oxidize to the corresponding carbonyl compound when reacted with chromic acid or Jones reagent? a) 2,2 - dimethyl propanol b) 2-methyl - 3 - pentanol c) 3,3 - dimethyl -2- pentanol d) 3-methyl - 3 - hexanol 15. Arrange the following alcohols in order of increasing boiling point: (CH_3)_3COH, CH_3(CH_2)_4OH. (CH_3)_3CCH_2OH, and (CH_3)_2CHCH_2CH_2OH. 16. Label each of the following reactions (one label per reaction) from the following categories: A. Tosylation B. Reduction C. Esterification D. Oxidation E. Substitution F. Dehydration

Explanation / Answer

13) C

14) D

15) CH3(CH2)4OH>(CH3)2CHCH2CH2OH>(CH3)3CCH2OH>(CH3)3COH

16) a - C Estirification

     b --- F dehydration

    c------A tosylation

d-------F dehydration

e ------E substitution

f -----Oxidation

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