McMurry FOC7e CH04有机双语.doc

Chapter 4 - Reactions of Alkenes and Alkynes1.Rank the carbocations below in order of increasing stability (least stable = 1; most stable = 3). Place the number corresponding to the carbocations relative stability in the blank below the structure.ANS:2.Alkene chemistry is dominated by what type of reaction?a.substitutionb.electrophilic additionc.nucleophilic additiond.eliminatione.both b and cANS:B3.Predict the major organic product(s) in the reaction below. If more than one major organic product is expected, draw each one.ANS:4.Predict the major organic product(s) in the reaction below. If more than one major organic product is expected, draw each one. Explain the significance of 35C and ether shown in the reaction.ANS:35C and ether are notes related to the reactions conditions. The reaction is carried out at 35C and the solvent is ether.5.The following reaction is carried out in cyclohexane with the application of heat. Write the complete equation for the reaction below. If more than one major organic product is expected, draw each one.ANS:6.What alkene would you use to prepare the following alkyl halide?ANS:Only one alkene would be possible:Instructions: Predict the structure of the alkene you would use to prepare the folloiwng compounds. There may be more than one answer in some cases.7.Predict:ANS:8.Predict.ANS:9.Predict.ANS:10.Predict. ANS:11.The product(s) of the reaction when carried out in an organic solventwould be:a.cis-1,2-dibromocyclohexane onlyb.trans-1,2-dibromocyclohexane onlyc.50/50 mixture of cis-1,2-dibromocyclohexane and trans-1,2-dibromocyclohexane onlyd.mixture with 50% being trans-1,2-dibromocyclohexane onlyANS:BInstructions: The reaction of 2-methylpropene with HBr in ether gives one of the two products below. Answer the following question(s) about this reaction.12.Refer to instructions. The reaction mixture would contain a majority of which isomeric product?ANS:Product B13.Refer to instructions. Which product is the Markovnikov product?ANS:Product B14.Predict the major product of the following reaction.ANS:Instructions: To answer the question(s) below, consider the following reaction:When cyclohexene reacts with chlorine in tetrachloromethane, the following dihalide is formed.15.Refer to instructions. Since the two chlorine atoms add to opposite faces of the cyclohexene double bond, we say that the reaction occurs with:a.syn stereochemistryb.cis stereochemistryc.anti stereochemistryd.retention of stereochemistryANS:c16.Refer to instructions. Provide the IUPAC name for the product of this reaction.ANS:trans-1,2-dichlorocyclohexaneInstructions: Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.17.Predict and indicate:ANS:18.Predict and indicate.ANS:19.Predict and indicate.ANS:20.Predict and indicate.ANS:21.Predict and indicate.ANS:22.Predict and indicate.ANS:23.Predict and indicate.ANS:24.Predict and indicate.ANS:25.On the structures provided, draw arrows showing the electron flow in the reaction mechanism for the electrophilic addition of hydrogen bromide to hex-1-yne.ANS:26.What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a bromoalkane?a.carbocationb.carbanionc.radicald.cyclic bromonium ionANS:A27.What type of reactive intermediate is involved in both of the following general reaction types?1)reaction of an alkene with Br2 in the presence of water to give a bromohydrin2)two-step hydroxylation of an alkenea.carbocationb.carbanionc.radicald.cyclic bromonium ione.cyclic ionANS:E28.What type of reactive intermediate is formed in the reaction of an alkene with aqueous acid to give an alcohol?a.carbocationb.carbanionc.radicald.carbeneANS:A29.What type of reaction mechanism accounts for the reaction of an alkyne with HBr to give an alkyl bromide?a.nucleophilic additionb.electrophilic additionc.radical additiond.eliminationANS:B30.What type of reaction mechanism accounts for the reaction of an alkene with HBr to give an alkyl bromide?a.nucleophilic additionb.electrophilic additionc.radical additiond.eliminationANS:B31.Complete the following reaction ANS: 32.Draw the structure of the monomer used to prepare the polymer shown below.ANS:33.Draw the structure of the polymer formed from the monomer given below, showing four repeating units.ANS:34.Circle whichever of the following would be classified as a conjugated diene.ANS:35.Draw all the isomeric products formed from the addition of HCl to the following compound. ANS:MATCH each definition to the term it describes. Place the letter of the term in the blank to the left of the definition.A.Cahn-Ingold-Prelog RulesB.Markovnikovs Rule36.Refer to Instructions. _Predicts that in electrophilic additions to alkenes the more stable carbocation intermediate is formed.ANS:B37.Refer to Instructions. _Assigns priorities to substituent groups on a carbon.ANS:A38.Refer to Instructions. _Predicts that in addition of HX to alkenes, the H adds to the less substituted alkene carbon and the X adds to the more substituted alkene carbon.ANS:B39.Draw two resonance structures for the species below.ANS:40.Draw two resonance structures for the species below.ANS:To answer the questions below, consider the following information:In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the label Compound A: C7H12. Government agents have offered you a considerable sum to determine the structure of this compound. After verifying the molecular formula by elemental analysis, you find that Compound A reacts with 1 mol equiv of hydrogen and, after treatment with acidic KMnO4, gives the dicarboxylic acid C (see below). Another bottle from the same laboratory is labeled Compound B (isomer of A). Compound B also reacts with 1 mol equiv of