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Arrange the following compounds in decreasing (highest to lowest) order of boiling point. Highest boiling on the left.  1-pentanol                         hexane                   1-pentanamine                     butyl methyl ether         I                                        II                                 III                                           IV    

When 2-methylcyclohexanone is treated with catalytic base in excess D2O, how many deuterium atoms become incorporated in the organic compound?

What is the major alkene formed in the following reaction?     

What is the product of the following reaction?    

Many nucleophilic addition reactions of aldehydes and ketones are catalyzed by acid or base. Bases catalyze hydration by: a. making the carbonyl group more electrophilic b. shifting the equilibrium of the reaction c. making the carbonyl group less electrophilic d. converting the water to hydroxide ion, a much better nucleophile

What is the major alkene formed in the following Hofmann elimination?   

α,β-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the β carbon, as shown below. This reaction is called _____ reaction. a. a 1,4-conjugate addition. b. an electrophilic addition. c. a direct addition d. a 1,2-addition.

Which of the following must be converted into a carboxylic acid through nitrile hydrolysis rather than through a Grignard synthesis with Mg/ether followed with dry CO2 and work-up with H3O+?

Which pair of reagents would produce the highest yield of (R)-2-ethoxybutane?

The α-halogenation of cyclohexanone ________.