11-22 - What is the best solvent for performing the...

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Unformatted text preview: 11/24/2010 What is the best solvent for performing the following reaction? How do solvents facilitate organic reactions? R H O R H OR OH H H O R H H C H H C H C H O C H H HO R O H K R ⊕ HH O H H H OH OH O H H HO HO H H R K ⊕ H R O H H C H H O C H HH C H C H H R RO R O R O R OR OR K R ⊕ R A B C H O R How do solvents facilitate organic reactions? R H O R H OR OH H H O R Are polar protic solvents the best solvents for performing SN2 reactions? A. yes B. no H H C H H C H C H O C H H HO R O H K R ⊕ HH O H HO HO H H H OH OH K H R ⊕ H R O H H C H H O C H HH C H C H H R RO R O R O R OR OR K R ⊕ R H O R protic polar aprotic polar Aprotic Aprotic polar solvents dissolve the ionic compound but do not solvate the nucleophile. Aprotic polar solvents do not solvate the nucleophile but they dissolve the ionic compound. N C H H Br protic protic polar aprotic polar energy reaction 1 11/24/2010 Why does the following reaction fail to produce a product? No Reaction 100% A. Cyanide ion does not react with 1˚ alkyl bromides. B. C. Potassium cyanide is insoluble in acetonitrile. Acetonitrile is a polar protic solvent that is not suitable for this type of reaction. Why does the above reaction succeed? Why can’t potassium ions pass through cell membranes? H H H O O H O H H H O H H O O H H H A. It is too large. B. Nothing, including potassium ions, ever pass through cell membranes. C. Potassium is not soluble in the hydrophobic region. K K ⊕ ⊕ outside a cell lipid bilayer outside a cell hydrophylic inside a cell hydrophobic inside a cell monensin monensin K ⊕ K ⊕ outside a cell outside a cell inside a cell inside a cell 2 11/24/2010 monensin-potassium complex K ⊕ K ⊕ outside a cell outside a cell inside a cell inside a cell K ⊕ What amino acid residues would be anticipated to be on the inside of the potassium channel? O Why are ethers good solvents for organolithiums? A. CH CH C CH2 C O OH O H N O B. CH C CH2 H N outside a cell Li R RO RO R R O R R OR OR Li O R ⊕ R R H H C O C H HH C H C H H inside a cell H H Why cannot alcohols be used for organolithiums? Choose the order that has the following compounds correctly arranged with respect to increasing solubility in water. O H H H H C H H C H C H O C H H H C H H C HH H H C C H H H H C H H H H C H O O H H C C H H H H O H H C HH C C H HH C C H HH i Li H HH HH O H ii iii C. ii < i < iii increasing solubility increasing solubility pKa = 16 pKa = 25 A. i < ii < iii increasing solubility increasing solubility B. i < iii < ii increasing solubility increasing solubility D. ii < iii < i E. iii < ii < i F. iii < i < ii 3 11/24/2010 How are these compounds named? Name the following aromatic alcohol. H H C H H C H C H O C H H H butyl alcohol butan ol H C H H C H C H O C H H HH HH OH H C H H C HH H O C H H C H H OH H H C H H C HH O C H H C H H diethyl ether Choose an acceptable name for the aromatic alcohol. How are these compounds named? H H C H H C H C H O C H H H H H C C H H O C H H A. 5-phenyl-3-decene B. phenylpentanol C. 2-phenylhexanol D. 2-phenyl-4-penten-2- ol E. 5-phenyl-3-decenol C H HH HH 2-phenyl-4-penten-2- ol OH H C H H H O C HH C H H C H H OH H C H H C HH H O C H H C H F. 5-phenyl-3-pentene H Choose the order that has the following compounds correctly arranged with respect to increasing boiling point. H H C H H C HH H C C H H O H H H H C H H H H C HH H O C H H C H H Choose the order that has the following compounds correctly arranged with respect to increasing boiling H H H HH point. H H O H C H HH C C H C H C H HH H C C H H H H C H C HH C C HH C C H H H C H H C H C H O C H H H C H H O H C H HH C C H HH C C δC H δ+ H δH H H H HH δ+ C O C C C HH H H O- H C i A. i ii iii D. ii iii i ii HH HH iii C. ii i iii HH H H H C H H H increasing boiling point increasing boiling point B. i iii ii E. iii ii i increasing boiling point increasing boiling point increasing boiling point increasing boiling point F. iii i ii 4 11/24/2010 Which of the following reactions would not give ethanol as a product? A. B. C. D. E. 1. Hg(OAc)2 H2C CH2 2. BH4 BH4 O H3C C H CH3CH2OH 1. BH3:THF 2. H2O2, OH H , H2O H2C CH2 H2C CH2 H2C CH2 OH H2O 5 ...
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