chem237_final_pkt_pt2 - CHEM237: Final Exam - Study Packet...

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2. A. Starting from propyne and a;ly other reagents. how would you prepare 2-pentyle? ( 10 points) H3CCGCCH2CH3 <----- B. from propyne, could you prepare 4.4-dimethyl-2-pentyne by the same type of reaction? If not. show what the products of an attempt to synthesize 4.4-dimethyl-2-pentyle by this type of reaction would be. (10 7. A. A hydrocarbon has the fo& CgH1o Could it be a bicycloalkane' a saturated cycloalkwe? q cyclic alkene? & acyclic alkene? an acycLic dime , atyclic albe? a cyclic diene? Circle aU the answers that fit ule data. (5 B. The hydrocarbon is found to decolorize bromine in the dark. Which of vour circled answers in Part A consistent with fact? ,C. he hydocarbon found to take rip exactly one mole of Hs on hydro- genation over a Pt catalyst which of your circled answers A consistent with fact? (5 D. On ozonolysis of the hydrocarbon. cy&op&ntanone and formaldehyde are formed. Draw the structure of the hydrocarbon (5
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1. Suppose that R-x a' reacr mm NU- via either an SNI /E 1, or an SN2 State whether the rate of reaction by each pathway wa be mcreased. deceasd, or lefl Largely unmged following cnanges-.~ way reactfon is carried out 118 points). A. IncreAsing tbe concenmtion Nu- SN1 /El SN~ B. Increasing the polaritv solvent. . C. Changing R from secondary -1 group to a tertiary alkyl group. 4, Addition of HBr alkene can occur by a free-radical chain reaction, initiated by perofides. ROOR Write the mechanism- of the free radical addition of HBr to propene. Label initiation and propagation . steps. You need. not show'-the chain terminating ste~s. (20 points) -.
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5. When E- and Z-2-butene react with peracids. trm- and cis-1.2-dimethyl- o*anes are formed. stereospeciflca-lly. A Draw and Label these two axiranes. (7 points) B. Why can the tmns-oxlrane be separated into two isomers. which show equal magnitudes but opposite signs of rotation: whereas, the cis-oxirane cannot be two such isomers? (5 points1 C. when optically active trans-oeane LS auowed to react with H2S04/H20. the butane-2.3-diol that is formed shows no optical activity.
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This note was uploaded on 12/15/2009 for the course CHEMISTRY 237 taught by Professor Anderson during the Spring '09 term at University of Washington.

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chem237_final_pkt_pt2 - CHEM237: Final Exam - Study Packet...

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