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UH CHEM 3331 - Exam 2 Study Guide
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CHEM 3331 1nd EditionExam # 2 Study Guide Lectures: 9-16Chapter 5 study questions1) For each structurea) Star any asymmetric carbon atomsb) Label each asymmetric carbon atom as (R) or (S)c) Draw any internal mirror planes of symmetryd) Label the structure as chiral or achirale) Label any meso compoundA.B.C.D.E.F.G.H.I.J.K.L.2) For each of the compounds described by the following names a) Draw a three dimensional representationb) Star each chirality centerc) Draw any planes of symmetryd) Draw any enantiomerse) Draw any diastereomersf) Label each structure as chiral or achiralA. (S)- 2-chlorobutaneB. (R)- 1,1,2- trimethyl-cyclohexaneC. (2R,3S)-2,3-dibromohexaneD. (1R,2R)-1,2- dibromo-cyclohexaneE. Meso-hexane-3,4-diol (CH3CH2CH(OH)CH(OH)CH2CH3)F. (+-)-hexane-3,4-diol3) Convert the following perspective formulas into fischer projections.A.B.C.D.4) Convert the following fischer projections into perspective formulas.A.B.C.D.5) Give the stereochemical relationship between each pair of structures. Same compound, structural isomers, enantiomers, or diastereomers.A.B.C.D.E.F.G.H.I.6) Draw the enantiomer, if any, for each structure.A.B.C.D.E.F.G.H.Chapter 61) Draw the structures for the following compound.A. Sec-butyl chlorideB. Isobutyl bromideC. 1,2-dibromo-3-methylpentaneD. 2,2,2-thrichloroethanolE. Trans-1-chloro-2-methyl-cyclohexaneF. Methylene chlorideG. ChloroformH. 1-chloro-1-isopropyl-cyclopentaneI. Tert- pentyl- iodide2) Predict the compound in each pair that will undergo the Sn2 reaction faster.A.B.C.D.E.F.3) Show how each compound might be synthesized by the Sn2 displacement of an alkyl halide.A.B.C.D.E.F.4) List the following carbocations in decreasing order of stability.5) Predict the products of the following Sn2 reactionsA.B.C.D.E.F.G.H.6) Predict the products of E1 reaction of the following compounds. Label the major products. A.B.C.7) Give a mechanism to explain the two products formed in the following reaction.8) Predict the major product of the following reaction, and give a mechanism to support your theory.9) Give mechanisms to account for the five products.10) Propose a mechanism to explain each product in the following reaction.Chapter 7 study questions1) Using cyclohexane as your starting material, show how you would synthesize each of thefollowing compounds.A. BromocyclohexaneB. CyclohexeneC. EthoxycyclohexaneD. 3-bromocyclo-1-eneE. Cyclohexa-1,3-dieneF. Cyclohexanol2) Draw a structure for each compound.A. 3-methylpent-1-eneB. Cis-3-methyl-3-hexeneC. 3,4-dibromobut-1-eneD. 1,3-cyclohexadieneE. Cycloocta-1,4-dieneF. (Z)-3-methyl-2-octeneG. VinylcyclopropaneH. (Z)-2-bromo-2-penteneI. (3Z,6E)- 1,3,6-octatriene3) Give a correct name for each compound.A.B.C.D.E.F.4) Label each structure as Z,E, or neither.A.B.C.D.5) Propose mechanisms for the following reactions.A.B.C.6) Propose a mechanism for the pinacol rearrangement. 7) Predict the products of the following eliminations of vicinal dibromides with potassium iodide (consider geometric constraints of E2 reactions).A.B.C.D.8) Determine which compounds show cis-trans isomerism.A. Pent-1-eneB. Pent-2-eneC. Hex-3-eneD. 1,1-dibromopropeneE. 1,2- dibromopropeneF. 1-bromo-1-chlorohexa-1,3-dieneAnswers and ExplanationsChapter 51)2)3)4)5)6)Chapter 61)2)3)4)5)6)7)8)9)10)Chapter


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UH CHEM 3331 - Exam 2 Study Guide

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