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Practice Problem Set #1

Practice Problem Set #1 - Wan—"4n 1.” «Jamaica...

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Unformatted text preview: Wan—"4n 1...” .. «Jamaica Qumms: 95.5. W Effie/2cm ii 1 Section 1. Multiple Choice. (24 points). 1. Circle the more stable carbocation ofthe pair. ®C>CH3 me Jim C(grmmtc Séf’quU/‘FS.’ G) @jbficug (MS) 6C9}, V O)“ CH} (W3) <:>@.¢;33 200(19»; ‘ '20 .3 at; 20 ally/H; gig/g 2. According to M0 theory, in the allyl cation (CH2=CH-CH2+), the two JE- ' electrons reside in a molecular orbital with the following phasing. Circle the correct answer. WWMMMM fl @[email protected] @.©/©@d\ HgC—C_CH2 HZC—C—~CH2 ( H20 c———CH2 } i OGQ a G 00/ kwwwmww 3. Circle the strongest base among the compounds below. NaOH A H30-CECLi ( CH3CH2CH2cF® ONa mm- as)» 1 fi . Consilcflu rid/i; (if 3% GflfiJi/fifidfii (2620/ 4. The conjugated molecule 1,3,5-hexatriene (CH2=CH-CH=CH-CH=CH2) has 6 :1: molecular orbitals. Which of the three molecular orbitals shown below is the HOMO. ma am lamaléj " I Section 11. Drawing Structures. 5. Draw all of the reasonable resonance structures for the compound below. Circle the res ance structure that would be the major contributor to the . /,.«;,,:/ I; r j )1" 6. Draw all of the reasonable resonance structures for the compound below. Circle the resonance structure that would be the major contributor to the hybrid. Section 111. Complete the Reactions. Fill in the reactants, reagents, and / or products for the transformations below. Where appropriate, show the stereochemistry. 7. Section IV. Draw the Mechanism. (16 points). 8. Draw the "arrow-pushing" reaction mechanism for the transformation below. Cl Low Conc. High Temperature CI a) ~18? We 2. or W"“’" A/ _ l Sections V. Outline the Synthesis. 9. Outline a synthesis for the compound below using the indicated starting material as the only carbon source along with any other needed reagents. a ‘ ————————> ...
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