Multiple Choice Quiz

Multiple Choice Quiz

Multiple Choice Quiz


1		What is the name of the following compound?
			A)	Ethyl cyclohexyl ether
			B)	Hexyl propyl ether
			C)	1-Ethoxycyclohexane
			D)	Cyclohexyl propyl ether


2		Which of the following is a secondary alcohol?
			A)
			B)
			C)
			D)	CH₃OH


3		Alcohols have higher boiling points than alkanes of comparable molecular weight because of
			A)	hydrogen bonding.
			B)	diaxial interactions.
			C)	steric strain.
			D)	hyperconjugation


4		Which of the following has the highest boiling point?
			A)	CH₃–O–CH₃
			B)	CH₃–CH₂–OH
			C)	CH₃–CH₂–CH₃
			D)	CH₂=CH–CH₃


5		What is the correct name for the following compound?
			A)	(R)-1-methyl-1-cyclohexen-4-ol
			B)	(S)-1-methyl-2-cyclohexen-4-ol
			C)	(R)-4-methyl-4-cyclohexen-1-ol
			D)	(S)-4-methyl-3-cyclohexen-1-ol


6		Which is the correct IUPAC name for the following compound?
			A)	4-Isopropyl-1,1-dimethyl-1-pentanol
			B)	5-Isopropyl-1,1-dimethyl-2-hexanol
			C)	1,1,4,5-Tetramethyl-1-hexanol
			D)	2,5,6-Trimethyl-2-heptanol


7		A chemist attempted unsuccessfully to form iodoethane from ethanol using NaI. Why did the reaction fail?
			A)	I^– was not a good enough nucleophile.
			B)	A secondary or tertiary alcohol was needed.
			C)	^–OH is a poor leaving group.
			D)	Na⁺ was a poor counterion.


8		What is the product of the following reaction?
			A)
			B)
			C)
			D)


9		Which product is obtained when (R)-2-butanol is treated with p-toluenesulfonyl chloride?
			A)	(R)-2-Butyl tosylate
			B)	(S)-2-Butyl tosylate
			C)	dl-2-Butyl tosylate
			D)	dl-2-Butanol


10		What is the leaving group in an S_N2 displacement of an alkyl tosylate with sodium iodide?
			A)	p-toluenesulfonic acid
			B)	toluenesulfonate anion
			C)	sulfate anion
			D)	acetate anion


11		Give the major product of the following reaction.
			A)
			B)
			C)
			D)


12		What is the product of the following reaction?
			A)
			B)
			C)
			D)


13		What is the major product formed in the following synthesis?
			A)
			B)
			C)
			D)


14		Which of the following will NOT convert 1-butanol into 1-chlorobutane in one step?
			A)	SOCl₂
			B)	PCl₃
			C)	HCl
			D)	CCl₄


15		What is the first step of the mechanism for the conversion of ethanol into bromoethane using PBr₃?
			A)	Bromide ion attacks the alcoholic carbon, displacing OH^–.
			B)	The alcohol hydroxide group leaves, forming a carbocation.
			C)	The alcohol oxygen attacks phosphorus, driving out bromide ion.
			D)	One PBr₃ bromine attacks the hydroxyl hydrogen.


16		Which reagent would be best for the conversion of tert-butanol into tert-butyl bromide?
			A)	PBr₃
			B)	HBr
			C)	NaBr
			D)	Br₂, NaOH


17		Give the expected major product of the following reaction.
			A)	recovered starting material (no reaction)
			B)
			C)
			D)


18		What is the major product of the following reaction?
			A)
			B)
			C)
			D)


19		The Williamson ether synthesis produces ethers by reacting an
			A)	alcohol with a metal.
			B)	alkoxide with a metal.
			C)	alkoxide with an alkyl halide.
			D)	alkyl halide with an aldehyde.


20		In which case would a Williamson ether synthesis fail?
			A)	sodium ethoxide + iodomethane
			B)	sodium ethoxide + iodoethane
			C)	sodium ethoxide + 2-iodopropane
			D)	sodium ethoxide + 2-iodo-2-methylpropane


21		Which of the following reagents should be used to prepare tert-butyl ethyl ether?
			A)	tert-butyl bromide and sodium ethoxide
			B)	tert-butyl alcohol and ethyl bromide
			C)	tert-butyl alcohol and ethanol
			D)	potassium tert-butoxide and ethyl bromide


22		Which of the following reagents should be used to prepare tert-butyl propyl ether?
			A)	2-methylpropene and 1-propanol
			B)	2-methylpropene, acetic acid and 1-propanol
			C)	2-methylpropene, H₂SO₄ and 1-propanol
			D)	1-propyl bromide and tert-butyl alcohol


23		Ethers may be used as solvents because they react only with
			A)	acids
			B)	bases
			C)	oxidizing agents
			D)	reducing agents


24		What are the products when ethyl isopropyl ether is cleaved with concentrated HI?
			A)	ethanol and 2-iodo-2-methylpropane
			B)	ethanol and 2-methylpropane
			C)	iodoethane and isopropyl alcohol
			D)	iodoethane and 2-methylpropane


25		What are the products when tert-butyl ethyl ether is cleaved with concentrated HI?
			A)	iodoethane and tert-butanol
			B)	iodoethane and 2-iodo-2-methylpropane
			C)	ethanol and 2-iodo-2-methylpropane
			D)	ethanol and tert-butanol


26		Which pair of products would result from the acid cleavage of tert-butyl propyl ether with excess concentrated HBr at an elevated temperature?
			A)	tert-butyl bromide and propyl alcohol
			B)	tert-butyl bromide and propyl bromide
			C)	tert-butyl alcohol and propyl bromide
			D)	2-methyl-2-butene and propyl bromide


27		Which pair of products would result from the acid cleavage of phenyl propyl ether with excess concentrated HBr at an elevated temperature?
			A)	Phenol and 1-propanol
			B)	Bromobenzene and 1-propanol
			C)	Bromobenzene and 1-bromopropane
			D)	Phenol and 1-bromopropane


28		Give the expected major products of the following reaction.
			A)	recovered starting material (no reaction)
			B)
			C)
			D)


29		What is the major product of the following reaction?
			A)
			B)
			C)
			D)


30		Which product is obtained by the acid-catalyzed ring-opening (H₃O⁺) of cis-2,3-diethyloxirane?
			A)	(3R,4S)-3,4-hexanediol
			B)	(3R,4R)-3,4-hexanediol
			C)	(3R,4S)-3,4-hexanediol and (3R,4R)-3,4-hexanediol
			D)	(3R,4R)-3,4-hexanediol and (3S,4S)-3,4-hexanediol

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