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All Textbook Solutions for Organic Chemistry: A Guided Inquiry

8E 9E 10E 11E 12E 13E 15E 16E 17E 18E 19E 20E 21E Double bonds do not rotate freely under normal conditions. The change from Z to E requires areaction. This can occur in the presence of a catalyst or with the addition of a large amount ofenergy (e.g., at high temperature). One such reaction is diagramed below: (1) Add enough potential energy to break the double bond (Eact) . (2) free rotation occurs at high energy transition state, then (3) reforming the double bond as a mixture of Z and E. Draw E-2-butene in one box and Z-2-butene in the other box, and explain your reasoning.up an example (not appearing in this ChemActivity) of a pair of molecules that are a)constitutional isomers, b) conformers. c) configurational stereoisomers.24E 25E 1CTQ 2CTQ 3CTQ Draw wedge and dash skeletal representations of cis and trans 1,3-dimethylcyclopentane.Label each ring in Figure 7.2 cis or trans.6CTQ 7CTQ 8CTQ a model of cyclohexane in a chair conformation, and explain why the names “axial” and“equatorial’ are appropriate.10CTQ 11CTQ Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.13CTQ 14CTQ 15CTQ 16CTQ 17CTQ 18CTQ Draw chair representations of cis-1-tert-butyl-4-methylcyclohexane and trans-1-tert-buty1-4-methylcyclohexane in the their lowest PE conformations.Which stereoisomer in the previous question is lower in PE? Explain your reasoning.21CTQ 1E Label each of the following as cis, trans or neither. Below each structure that is cis draw a transconfigurational stereoisomer or vice versa.Which pair has more in common with one another?4E 5E 6E Fill in the table by drawing a representation of a cis and a transconfigurational stereoisomer foreach row. Show each molecule in its lowest potential energy chair conformation.9E True or False: If you perform a chair flip on cis-1,4-dichlorocyclohexane, the result is still called cis-1,4-dichlorocyclohexane.11E 12E 13E 14E 15E Draw trans-1-tert-butyl-3-methylcyclohexane in its most favorable chair conformation, andexplain your reasoning.Build a model of methylcyclohexane, and use the model to complete the following Newmanprojections of methylcyclohexane in the chair conformation: a. When the methyl group is in an axial or equatorial (circle one) position, the molecule is inits lowest potential energy conformation. b. Label one Newman projection above anti and the other gauche to describe the relationshipbetween the methyl group and C3 of the ring. c. In general, which is a lower PE conformation, anti or gauche? d. Explain how your answer to b and c provide an explanation for why it is more favorable fora large group to be in an equatorial than an axial position.A student names the second structure above 2,3-dimethylcyclohex-1-ene. What rule does thisviolate?2CTQ Name each of the following alkenes:Draw the following alkenes: a. 2,3-dimethylbut-2-ene b. cyclopenta-1,3-diene c. penta-2,3-diene 5CTQ 6CTQ 7CTQ 8CTQ 9CTQ 10CTQ Instead of using the ending “ol,” an OH can be treated like a substituent or halogen using the term“hydroxyl.” For example, hexane-2,4-diol can be called 2,4-dihydroxyhexane. Write anequivalent name for 1,2,3-cyclohexanetriol using the term “hydroxyl.”12CTQ 13CTQ 14CTQ 15CTQ 16CTQ 17CTQ 18CTQ 19CTQ 20CTQ 21CTQ 1E 2E 1CTQ 2CTQ 3CTQ 4CTQ 5CTQ 6CTQ 7CTQ 8CTQ 9CTQ 10CTQ Draw the products that result from the electron movements shown using curved arrows in Fig. 8.2.12CTQ Draw the products that would result if the arrow “bounced” toward the other carbon.14CTQ What information (if any) from the following energy diagram confirms your answer to theprevious question?16CTQ 17CTQ The reactants, intermediates, final products, and all curved arrows showing bonds forming andbreaking are collectively referred to as the mechanism of a reaction. For the following reactants: a. Explain why the original statement of Markovnikov’s rule does not help in this case, but themodern restatement of Markovnikov’s rule tells you which carbon will get the X (Cl). b. Show the mechanism of the most likely addition reaction between the reactants.19CTQ 20CTQ 21CTQ 22CTQ Explain how you can tell from the energy diagram that the reaction with the catalyst in Fig. 8.4 isfaster than the reaction without the catalyst.Explain why the following mechanism for hydration of an alkene cannot occur.25CTQ 26CTQ 27CTQ 28CTQ 29CTQ 30CTQ 31CTQ The hydration above is one of a family of reactions called electrophilic addition reactions.Explain why electrophilic addition is an appropriate name for this reaction.33CTQ Which statement is false? a. A mechanistic step may include many synthetic steps. b. A synthetic step may include many mechanistic steps.35CTQ 36CTQ 37CTQ Draw the complete mechanism including the intermediate and most likely product for each reaction.2E Explain why ethene does not react with HX ( X=Cl , Br or I) under normal conditions.Draw the complete mechanism of each pair of reactants including any favorable rearrangements and all important resonance structures of all intermediates. a. Which reaction has a lower PE carbocation intermediate? b. Draw an energy diagram showing the reaction profiles of both reactions in the previous question. Use a dotted line for the first pair of reactants and a solid line for the second pair of reactants. (Assume the energy of the starting materials and products are the same for both pairs and the reactions are neither uphill nor downhill on net. c. Mark points on the energy diagram corresponding to each carbocation in your mechanisms.5E 6E 7E 8E 9E 10E 11E 12E 15E A student proposes the following reaction mechanism for the reaction in Model 6. Which step inthis mechanism is least favorable? Explain your reasoning.17E 18E 19E 1CTQ The Br produced by the reaction in Figure 9.2 could combine with the carbocation you drew to give a dibromide product (a product with two Br atoms). Use a curved arrow to show the Br making a bond to the carbocation, and draw the resulting dibromide product.3CTQ 4CTQ 5CTQ 6CTQ 7CTQ 8CTQ 9CTQ 10CTQ 11CTQ 12CTQ In a synthetic transformation, reagents that must be added in separate steps are written over differentsynthetic-step reaction arrows, or given different step numbers, or both.14CTQ 1E 2E 3E 4E 5E 1CTQ 2CTQ 3CTQ 4CTQ 5CTQ 6CTQ 7CTQ 8CTQ 9CTQ 10CTQ 11CTQ 12CTQ 13CTQ 14CTQ 15CTQ 16CTQ 17CTQ 18CTQ 19CTQ 20CTQ 21CTQ 22CTQ 23CTQ 24CTQ 25CTQ 1E 2E 3E 4E 5E 6E 7E 8E 10E 11E 12E 13E 1CTQ 2CTQ 3CTQ 4CTQ 5CTQ 6CTQ 7CTQ 8CTQ 9CTQ 10CTQ 11CTQ 12CTQ 13CTQ 14CTQ 1E 2E 3E 4E 5E 1CTQ 2CTQ 3CTQ 4CTQ 5CTQ 6CTQ 7CTQ 8CTQ 9CTQ 10CTQ 11CTQ 12CTQ 13CTQ 14CTQ 15CTQ 16CTQ 17CTQ 18CTQ 19CTQ 20CTQ 21CTQ 22CTQ 23CTQ 24CTQ 25CTQ 26CTQ 27CTQ 28CTQ 29CTQ 30CTQ 31CTQ 32CTQ 33CTQ 34CTQ 35CTQ 36CTQ 37CTQ 38CTQ 39CTQ 40CTQ 41CTQ 42CTQ 1E 2E 3E 4E 5E 6E 7E 8E 9E 10E 11E 12E 13E 14E 15E 16E 17E 18E 19E 20E 21E 1CTQ 2CTQ 3CTQ 4CTQ 5CTQ 6CTQ 7CTQ 8CTQ 9CTQ 10CTQ 11CTQ 12CTQ 13CTQ 14CTQ 15CTQ 16CTQ 17CTQ 18CTQ 19CTQ 20CTQ 21CTQ 22CTQ 23CTQ 24CTQ 25CTQ 26CTQ 27CTQ 28CTQ 29CTQ 30CTQ 31CTQ

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