Substitution and Oxidation of Alcohols

Draw the product of another reaction that 2-methyl-2-propanol might undergo in strong H₂SO_4.

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A positive test with Jones Reagent indicates that a compound undergoes oxidation whereas chromium (+6) undergoes reduction to chromium (+3). Which one of the following four-carbon alcohols does not undergo an easy oxidation to give a positive Jones test?

a. 1-butanol, CH3CH2CH2CH2OH

b. 2-butanol, CH3CHOHCH2CH3

c. 2-methyl-1-propanol, (CH3)2CHCH2OH

d. 2-methyl-2-propanol, (CH3)3COH

19. The IUPAC name for (CH3)3COH is _____. a. 2-butanol b. 2-methyl-2-propanol c. 2-propyl-2-butanol d. 2-methyl-1-porpanol e. 2,2-dimethyl-2-ethanol

24. Which of the following alcohols produces no reaction when subjected to oxidation? a. methanol b. 2-methyl-2-propanol c. 2-propanol d. 3,4-dimethyl-1-pentanol e. 2-butanol

13. Which of the following alcohols is the active ingredient in most alcoholic beverages? a. Methyl alcohol b. Ethyl alcohol c. Isopropyl alcohol d. Butyl alcohol e. Cyclohexanol

Draw the structure and name the product formed if the following alcohols are oxidized. Assume an excess of the oxidizing agent is used. If the alcohol is not expected to react with a chemical oxidizing agent, write NR (no reaction).

(a) CH₃CH₂CH₂CH₂OH

(b) 2-butanol

(d) 2-methyl-1-propanol