O Chem Final – Flashcards
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What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide? (R) 1-cyano-4-methylhexane (S) 1-cyano-4-methylhexane (R) 4-methyl-1-hexene (S) 4-methyl-1-hexene
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(R) 1-cyano-4-methylhexane
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Which of the following statements is not true regarding SN2 reactions? A carbocation intermediate is formed. The mechanism has only one step. Aprotic solvents are good choices for SN1 reactions. The stereochemical outcome is inversion at the carbon bearing the leaving group.
answer
A carbocation intermediate is formed.
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The reaction of tert-butyl bromide, (CH3)3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3)3COCH3. What is the effect of doubling the concentration of methanol on the rate of the reaction?
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Stays the same
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Which of the following sets consists of only polar protic solvents? water, DMF, DMSO acetic acid, methanol, water DMSO, ethanol, acetonitrile DMF, acetonitrile, DMSO
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acetic acid, methanol, water
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Which of the following statements is not true regarding SN1 reactions? A carbocation intermediate is formed. The mechanism has only one step. Polar, protic solvents are good choices for SN1 reactions. The stereochemical outcome is racemization at the carbon bearing the leaving group.
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The mechanism has only one step.
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Which of the following has the highest boiling point? pentane methyl propyl ether diethyl ether 1-butanol
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1-butanol
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Which of the following is not a characteristic of SN2 reactions? the electrophilic carbon undergoes inversion of stereochemistry the rate is proportional to the concentration of substrate the rate is proportional to the concentration of nucleophile the rate is independent of the solvent
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the rate is independent of the solvent
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Which of the following anions is the best leaving group in an SN1 reaction? F- HO- NH2- Cl-
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Cl-
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What is the major organic product obtained from the reaction of 2,2-dimethyl-1-propanol aqueous HBr at reflux? 1-bromo-2,2-dimethylpropane 1-bromo-2-methylbutane 2-bromo-2-methylbutane 3-bromo-2-methylbutane The correct product is not listed.
answer
2-bromo-2-methylbutane
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What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with HCl to give tert-butyl chloride? tert-butyl radical tert-butyl anion tert-butyl cation tert-butoxide
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tert-butyl cation
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What type of reactive intermediate is formed in the reaction of methyl propene with methanol in the presence of an acid catalyst to give methyl tert-butyl ether (MTBE)? tert-butyl cation tert-butyl radical tert-butyl anion tert-butoxide
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tert-butyl cation
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Which of the following ethers cannot be prepared by a Williamson ether synthesis? tert-butyl phenyl ether isopropyl methyl ether anisole tert-butyl methyl ether
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tert-butyl phenyl ether
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What is the major organic product obtained from the reaction of 2,2-dimethyl-1-propanol aqueous HBr at reflux? 1-bromo-2,2-dimethylpropane 1-bromo-2-methylbutane 2-bromo-2-methylbutane 3-bromo-2-methylbutane
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2-bromo-2-methylbutane
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Which of the following statements are true? 1. ethanol is more soluble in water than dimethyl ether 2. ethanol has a higher boiling point than dimethyl ether 3. ethanol has the same molecular weight as dimethylether only 1 only 1 and 2 only 1 and 3 1, 2 and 3
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1, 2, and 3
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What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with H2SO4 to give methylpropene? tert-butyl cation tert-butyl anion tert-butyl radical tert-butoxide
answer
tert-butyl cation
