Chem 008 Quiz 10

Chem 008 Quiz 10 - D) 1. CH3CH2CH2Li 2. HBr E) 1. H3PO4, ....

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Sheet1 Page 1 Chem. 8 Quiz 7 Name ___________________________________Name ____________________________________ Q1-2 points “ Show how 1-propanol can be converted into CH3CH2CH2SCH2CH3 by means of a sulfonate ester. You only need to indicate the sequence of reagents. 1. TsCl/pyridine CH3CH2CH2OH CH3CH2CH2SCH2CH3 2. CH3CH2SCan be shown in two steps but that is not necessary. Q2-2 points -Label the following alcohols in order of decreasing rate of dehydration in the presence of acid. Write 1 under the fastest, 2 under the second fastest and 3 under the slowest HO OHOH 12 3 Q3-3 points “ Circle the major reaction product of 3,3-dimethyl-2-butanol with HBr and explain the mechanism for obtaining it. BrBrBrBrAns: SN1 with a 1,2-alkyl (or methyl) shift Q4-2 points “ Which of the following sequences of reactions would be best when converting into ? O A) 1. CH3CH=CHNa 2. H3O+ B) 1. CH3CH2CH2MgBr 2. H2SO4, . C) 1. H3O+ 2. CH3CH2CH2Na
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Unformatted text preview: D) 1. CH3CH2CH2Li 2. HBr E) 1. H3PO4, . 2. CH3CH2CH2MgBr 3. H+ This involves the reaction of a Grignard reagent with the reactant to produce in the first step. OH The second step is a dehydration in which the OH is protonated and water leaves producing a secondary carbocation that undergoes a 1,2 methyl shift Sheet1 Page 2 to and then loses a + + proton to form the double bond. p Chem. 8 Quiz 7 Name ____________________________________ Name ____________________________________ Q5-1 point & Circle which of these alcohols from which a ketone can result from oxidation with chromate? OHOHOHOHOH Q6-2 bonus points -When 1-pentanol is heated with HCl/ZnCl2, 1-chloropentane is the major organic product. Is the reaction mechanism SN1, SN2, E1 or E2? Why is ZnCl2 used? Ans: SN2. Because Zn makes Cl-into a better nucleophile or they can just state that Cl-is not a strong nucleophile. n...
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This note was uploaded on 07/02/2010 for the course CHEM 008 taught by Professor Forman during the Spring '10 term at UCM.

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Chem 008 Quiz 10 - D) 1. CH3CH2CH2Li 2. HBr E) 1. H3PO4, ....

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