Textbook QuestionAfter a proton is removed from the OH group, which compound in each pair forms a cyclic ether more rapidly?c. <IMAGE>230views
Textbook QuestionPure (S)-2-bromo-2-fluorobutane reacts with methoxide ion in methanol to give a mixture of (S)-2-fluoro-2-methoxybutane and three fluoroalkenes. b. Propose a mechanism to show how (S)-2-bromo-2-fluorobutane reacts to give (S)-2-fluoro-2-methoxybutane. Has this reaction gone with retention or inversion of configuration?398views
Textbook QuestionPure (S)-2-bromo-2-fluorobutane reacts with methoxide ion in methanol to give a mixture of (S)-2-fluoro-2-methoxybutane and three fluoroalkenes. a. Use mechanisms to show which three fluoroalkenes are formed.711views
Textbook QuestionPropose mechanisms for the following reactions. Additional products may be formed, but your mechanism only needs to explain the products shown. (a) CH3OH, heat—> + + 1191views
Textbook QuestionWrite a balanced equation for each reaction, showing the major product you expect. (d) CH3CH(CH3)C(CH3)2Br NaOH, heat—>405views
Textbook QuestionPredict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely. h. 1-bromo-1-methylcyclopentane heated in methanol886views
Textbook QuestionPredict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely. g. 1−bromo−1−methylcyclopentane+NaOEt in ethanol936views1rank
Textbook QuestionPredict the major and minor elimination products of the following proposed reactions (ignoring any possible substitutions for now). In each case, explain whether you expect the mechanism of the elimination to be E1 or E2. a. NaOCH2CH3, CH3CH2OH heat——> 1300views
Textbook QuestionFor each reaction, decide whether substitution or elimination (or both) is possible, and predict the products you expect. Label the major products. a. 1−bromo−1−methylcyclohexane + NaOH in acetone781views
Textbook QuestionUnder second-order conditions (strong base/nucleophile), SN2 and E2 reactions may occur simultaneously and compete with each other. Show what products might be expected from the reaction of 2-bromo-3-methylbutane (a moderately hindered 2° alkyl halide) with sodium ethoxide. HINT: Zaitsev's rule usually applies in E2 reactions unless the base and/or the leaving group are unusually bulky.835views1comments
Textbook QuestionWhen (1-bromoethyl)cyclohexane is heated in methanol for an extended period of time, five products result: two ethers and three alkenes. Predict the products of this reaction, and propose mechanisms for their formation.1137views
Textbook QuestionGive the substitution and elimination products you would expect from the following reactions. a. 3-bromo-3-ethylpentane heated in methanol917views
Textbook QuestionWrite a balanced equation for each reaction, showing the major product you expect. (b) NaOC(CH3)3—> 744views
Textbook QuestionIf 2-fluoropentane could undergo an E1 reaction, would you expect the major product to be the more stable alkene or the less stable alkene? Explain your answer.702views1rank
Textbook QuestionFour alkenes are formed from the E1 reaction of 3-bromo-2,3-dimethylpentane and methanol. Draw the structures of the alkenes and rank them according to the amount that would be formed.973views
Textbook QuestionDraw the major elimination product that would be obtained from each of the following reactants with a strong base and with a weak base: a. 548views
Textbook Questiona. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol. b. Are all the products optically active?502views
Textbook QuestionFor each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield. d. trans-1-chloro-3-methylcyclohexane+high concentration of CH3O−334views
Textbook QuestionPredict the product for the following reaction and write a mechanism to explain how it is formed. 830views
Textbook QuestionDraw the products of each of the following SN2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed. a. (3S,4S)-3-bromo-4-methylhexane+CH3O−498views
Textbook QuestionFor each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield. c. trans-1-chloro-2-methylcyclohexane+high concentration of CH3O−604views
Textbook QuestionWhat product is formed when 1-bromopropane reacts with each of the following nucleophiles? d. HS−917views
Textbook QuestionWhat product is formed when 1-bromopropane reacts with each of the following nucleophiles? c. CH3S−535views
Textbook QuestionIdentify the three products formed when 2-bromo-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.728views
Textbook QuestionA small amount of another organic product is formed in a Williamson ether synthesis. What is this product when the alkyl halide used in the synthesis of butyl propyl ether is b. butyl bromide?375views
Textbook QuestionA small amount of another organic product is formed in a Williamson ether synthesis. What is this product when the alkyl halide used in the synthesis of butyl propyl ether is a. propyl bromide?316views
Textbook QuestionDraw the elimination products that are formed when 3-bromo-3-methyl-1-butene reacts with b. CH3OH548views
Textbook QuestionDraw the elimination products that are formed when 3-bromo-3-methyl-1-butene reacts with a. CH3O−.494views
Textbook QuestionFor each of the following reactions, (1) decide whether an E2 or an E1 occurs, and (2) draw the major elimination product: a. b. 658views
Textbook QuestionDraw the substitution and elimination products for the following reactions, showing the configuration of each product: a. trans-1-chloro-2-methylcyclohexane + CH3O−630views
Textbook QuestionDraw the substitution and elimination products for the following reactions, showing the configuration of each product: b. cis-1-chloro-2-methylcyclohexane + CH3O−343views
Textbook QuestionWhat products are formed when the following stereoisomer of 2-chloro-1,3-dimethylcyclohexane reacts with methoxide ion?340views
Textbook QuestionGiven the reactants shown, what type of elimination would you expect to occur? (a)310views
Textbook QuestionGiven the reactants shown, what type of elimination would you expect to occur? (d)286views
Textbook QuestionShow a mechanism for the following elimination reactions. Label the mechanism as E1 or E2. (a)402views
Textbook QuestionPaying close attention to the stereochemical outcome, predict the product of these elimination reactions. (a)286views
Textbook QuestionSuggest an appropriate base to synthesize the alkene as the major product from the starting haloalkane. (a)267views
Textbook QuestionWhich reaction, E2 or Sₙ2, would you expect to be more favorable at higher temperatures?334views
Textbook QuestionFor which of the following reactions would you expect elimination to be more favored than substitution? (f) vs.291views
Textbook Question(••) For each pair, choose the haloalkane that would react most quickly in an Sₙ1 or E1 reaction. (c) vs.363views
Textbook Question(••••) The following chlorocyclohexane undergoes neither Sₙ2 nor E2 under the conditions shown. Why?282views
Textbook Question(••) Identify whether each of the following reactions proceed by an S_N1 ,S_N2 , E1, or E2 mechanism. (a)310views
Textbook QuestionPredict the products of the following reactions. (c) benzyl bromide + sodium cyanide938views
Textbook Question(•••) Suggest a bromoalkane and the conditions necessary to produce the alkenes shown.(b) <IMAGE>269views
Textbook Question(••) Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.(d) 270views
Textbook QuestionSuggest an appropriate base to synthesize the alkene as the major product from the starting haloalkane.(b) 229views
Textbook QuestionGiven the reactants shown, what type of elimination would you expect to occur?(c) <IMAGE>278views
Textbook QuestionFor which of the following reactions would you expect elimination to be more favored than substitution?(c) <IMAGE>vs.<IMAGE>282views
Textbook Question(•••) Give a mechanism for the following substitution and elimination reactions.(c) <IMAGE>300views
Textbook Question(•••) Predict the product(s) of the following substitution or elimination reactions, paying close attention to the stereochemical outcome of the reactions.(g) <IMAGE>259views
Textbook Question(•••) Predict the product(s) of the following substitution or elimination reactions, paying close attention to the stereochemical outcome of the reactions.(h) <IMAGE>286views
Textbook Question(••) Predict the major product(s) of the following elimination reactions, paying close attention to the stereochemical outcome of the reactions.(f) <IMAGE>225views
Textbook QuestionWould you expect the following bases to favor E1 or E2 elimination?(c) <IMAGE>253views
Textbook QuestionWhich of the following SN2 and E2 reactions, respectively, is faster? Justify your choice.a. <IMAGE246views
Textbook QuestionWhich of the following SN2 and E2 reactions, respectively, is faster? Justify your choice.b. <IMAGE254views
Textbook QuestionFor which of the following reactions would you expect elimination to be more favored than substitution?(e) <IMAGE> vs. <IMAGE>273views
Textbook Question(••) For each pair, choose the haloalkane that would react most quickly in an Sₙ1 or E1 reaction. (a) <IMAGE> vs. <IMAGE> 234views
Textbook Question(••) Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (i) 1. BH₃ 2. NaOH, H₂O₂ (ii) 1. Hg(OAc)₂ 2. NaBH₄ (iii) H₂SO₄ , H₂O (iv) 1. OsO₄ 2. NaHSO₃ (v) H₂O (vi) NaOH, H₂O . If there is no reaction, write 'no reaction.'(f) <IMAGE>264views
Textbook Question(••) Identify whether each of the following reactions proceed by an S_N1 ,S_N2 , E1, or E2 mechanism.(c) <IMAGE>216views
Textbook Question(••) Identify whether each of the following reactions proceed by an SN1 ,SN2 , E1, or E2 mechanism.(b) <IMAGE>333views
Textbook QuestionFor which of the following reactions would you expect elimination to be more favored than substitution?(a) <IMAGE>vs.<IMAGE>215views
Textbook QuestionFor which of the following reactions would you expect elimination to be more favored than substitution?(d) <IMAGE>vs.<IMAGE>176views
Textbook QuestionWhen the following compound undergoes solvolysis in ethanol, three products are obtained. Propose a mechanism to account for the formation of these products.<IMAGE>246views
Textbook QuestionDraw the substitution and elimination products for the following reactions, showing the configuration of each product:c. 1-chloro-1-methylcyclohexane + CH3O−d. 1-chloro-1-methylcyclohexane + CH3OH234views
Textbook QuestionFor each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.a. (R)-2-bromohexane+high concentration of CH3O−b. (R)-3-bromo-3-methylhexane+CH3OH209views
Textbook QuestionExplain how each of the following changes affect the rate of the reaction of 1-bromobutane with ethoxide ion in DMF.c. The alkyl halide is changed to 1-chlorobutane.d. The alkyl halide is changed to 2-bromobutane.230views
Textbook QuestionDraw the products of each of the following SN2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.c. (3S,4R)-3-bromo-4-methylhexane + CH3O−201views
Textbook QuestionWhat products (including stereoisomers, if applicable) are formed from the reaction of 3-bromo-3-methylpentane:b. with H2O?229views
Textbook QuestionWhich of these reactions are likely to produce both elimination and substitution products?a. 2−bromopentane + NaOCH3b. 3−bromo−3−methylpentane + NaOMe. (Me=methyl,CH3)c. 2-bromo-3-ethylpentane + NaOH 281views
Textbook QuestionFor each reaction, decide whether substitution or elimination (or both) is possible, and predict the products you expect. Label the major products.c. chlorocyclohexane+NaOCH3 in CH3OHd. chlorocyclohexane + NaOC(CH3)3 in (CH3)3COH226views
Textbook QuestionSilver-assisted solvolysis of bromomethylcyclopentane in methanol gives a complex product mixture of the following five compounds. Propose mechanisms to account for these products.<IMAGE> AgNo3, CH3OH, heat—> <IMAGE>226views
Textbook QuestionDeuterium (D) is the isotope of hydrogen of mass number 2, with a proton and a neutron in its nucleus. The chemistry of deuterium is nearly identical to the chemistry of hydrogen, except that the C―D bond is slightly (5.0 kJ/mol, or 1.2 kcal/mol) stronger than the C―H bond. Reaction rates tend to be slower if a C―D bond (as opposed to a C―H bond) is broken in a rate-limiting step. This effect on the rate is called a kinetic isotope effect. (Review PROBLEM 4-57 <IMAGE>)a. Propose a mechanism to explain each product in the following reaction.CH3CH(Br)CH3 KOH, alcohol—> CH2=CH-CH3 elimination product + CH3CH(OH)CH3 substitution product 225views
Textbook Questiona. Two stereoisomers of a bromodecalin are shown. Although the difference between these stereoisomers may seem trivial, one isomer undergoes elimination with KOH much faster than the other. Predict the products of these eliminations, and explain the large difference in the ease of elimination.Fast elimination <IMAGE> slow elimination <IMAGE> 235views
Textbook QuestionMake models of the following compounds, and predict the products formed when they react with the strong bases shown.HINT: Anti-coplanar E2 eliminations are common.Syn-coplanar E2 eliminations are rare, usually occurring when free rotation is not possible.b. meso-1,2-dibromo-1,2-diphenylethane + (CH3CH2)3N:216views
Textbook QuestionPredict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.e. isobutyliodide+KOH in ethanol/waterf. isobutylchloride+AgNO3 in ethanol/water224views
Textbook QuestionThe solvolysis of 2-bromo-3-methylbutane potentially can give several products, including both E1 and products from both the unrearranged carbocation and the rearranged carbocation.Mechanisms 6-6 (page 282) <IMAGE> and 7-2 (previous page) <IMAGE> show the products from the rearranged carbocation.Summarize all the possible products, showing which carbocation they come from and whether they are the products of E1 or reactions.294views
Textbook QuestionFor each reaction, decide whether substitution or elimination (or both) is possible, and predict the products you expect. Label the major products.b. 1-bromo-1-methylcyclohexane + triethylamine(Et3N:)196views
Textbook QuestionGive the substitution and elimination products you would expect from the following reactions.b. 1-iodo-1-phenylcyclopentane heated in ethanol201views
Textbook QuestionPredict the major and minor elimination products of the following proposed reactions (ignoring any possible substitutions for now).In each case, explain whether you expect the mechanism of the elimination to be E1 or E2.b. <IMAGE> AgNO3, CH3OH heat——>168views
Textbook QuestionPredict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.a. 1−bromohexane+sodium ethoxide in ethanol228views
Textbook QuestionPredict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.b. 2−chlorohexane+NaOCH3 in methanol148views
Textbook QuestionWhen (±)−2,3−dibromobutane reacts with potassium hydroxide, some of the products are (2S,3R)-3-bromobutan-2-ol and its enantiomer and trans-2-bromobut-2-ene.Give mechanisms to account for these products.3 bromobutan-2-ol <IMAGE> <IMAGE>trans-2-bromobut-2-ene <IMAGE>185views
Textbook QuestionMake models of the following compounds, and predict the products formed when they react with the strong bases shown.HINT: Anti-coplanar E2 eliminations are common.Syn-coplanar E2 eliminations are rare, usually occurring when free rotation is not possible.c. (d,l)-1,2-dibromo-1,2-diphenylethane + (CH3CH2)3N:187views
Textbook QuestionMake models of the following compounds, and predict the products formed when they react with the strong bases shown.HINT: Anti-coplanar E2 eliminations are common.Syn-coplanar E2 eliminations are rare, usually occurring when free rotation is not possible.d. <IMAGE> + NaOH in acetone211views
Textbook QuestionPropose mechanisms for the following reactions. Additional products may be formed, but your mechanism only needs to explain the products shown.(c) <IMAGE> BrOH, heat—> <IMAGE> + <IMAGE> + <IMAGE>193views
Textbook QuestionDraw the products of each of the following SN2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.b. (3R,4R)-3-bromo-4-methylhexane+CH3O−175views
Textbook QuestionWhich of the following compounds would react faster in an<IMAGE><IMAGE>a. E1 reaction?b. E2 reaction?238views
Multiple Choice Which of the following is NOT a reason why the given elimination reaction is favorable? 350views
Open QuestionFor which of the following reactions would you expect elimination to be more favored than substitution?(c) <IMAGE>vs.<IMAGE>257views