Textbook QuestionWrite the rate law for the following reaction and identify which molecules are present in the rate-determining step. Draw a possible transition state and propose a mechanism.426views
Textbook QuestionPredict the major products of the following substitutions. e. 1-chloropentane + NaI —>642views
Textbook QuestionPredict the major products of the following substitutions. d. CH3CH2CH2I + NaCN —>697views
Textbook QuestionPredict the major products of the following substitutions. b. HC≡C:- Na+ sodium acetylide + 1-chlorobutane CH3CH2CH2CH2Cl —>604views
Textbook QuestionFor each pair of compounds, state which compound is the better SN2 substrate. a. 2-methyl-1-iodopropane or tera-butyl iodide. b. cyclohexyl bromide or 1-bromo-1-methylcyclohexane524views
Textbook QuestionPredict the products of the following SN2 reactions. e. + CH3I —> f. (CH3)3C—CH2CH2Br + excess NH3 —> 1051views
Textbook QuestionPredict the products of the following SN2 reactions. a. CH3CH2ONa + CH3CH2Cl —> b. + NaCN —> 1673views
Textbook QuestionPredict the compound in each pair that will undergo the SN2 reaction faster. (a) or (b) or 986views
Textbook QuestionDraw the substitution product formed by each of the following SN2 reactions: a. trans-1-iodo-4-ethylcyclohexane and methoxide ion b. cis-1-chloro-3-methylcyclobutane and ethoxide ion571views
Textbook QuestionDraw the products obtained from the SN2 reaction of: c. (S)-3-chlorohexane and hydroxide ion. d. 3-iodopentane and hydroxide ion.444views
Textbook QuestionWhich alkyl halide is more reactive in an SN2 reaction with a given nucleophile? c. d. 489views
Textbook QuestionRank the following alkyl bromides from most reactive to least reactive in an SN2 reaction: 1-bromo-2-methylbutane, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, and 1-bromopentane.546views
Textbook QuestionWhich alkyl halide is more reactive in an SN2 reaction with a given nucleophile? a. b. 355views
Textbook QuestionDoes increasing the energy barrier for an SN2 reaction increase or decrease the magnitude of the rate constant for the reaction?389views
Textbook QuestionThe rate of the reaction of methyl iodide with quinuclidine was measured in nitrobenzene, and then the rate of the reaction of methyl iodide with triethylamine was measured in the same solvent. The concentration of the reagents was the same in both experiments.a.Which reaction had the larger rate constant?170views
Textbook QuestionDraw a transition state for the following substitution reaction. H₃C―C ≡ C⁻ Na⁺ + H₃C―Cl → H₃C―C ≡ C―CH₃577views
Textbook QuestionPredict the major products of the following reactions. (a) ethyl tosylate + potassium tert-butoxide (b) isobutyl tosylate + NaI (c) (R)-2-hexyl tosylate + NaCN1066views
Textbook QuestionPractice your electron-pushing skills by drawing a mechanism for the following Sₙ2 reactions. (a)322views
Textbook QuestionPractice your electron-pushing skills by drawing a mechanism for the following Sₙ2 reactions. (b)346views
Textbook Question(••) For each pair, choose the haloalkane that would react most quickly in an Sₙ2 reaction. (b) vs.314views
Textbook Question(••) For each pair, choose the haloalkane that would react most quickly in an Sₙ2 reaction. (d) vs.361views
Textbook QuestionThe following reaction, though run under standard solvolysis conditions, occurs via an Sₙ2 reaction. Why?<IMAGE>278views
Textbook Question(•••) Crown ethers are able to solvate cations based on their size. Specifically, 15-crown-5 forms stable complexes with sodium. How would the addition of a crown ether change the rate of an Sₙ2 reaction?<IMAGE>256views
Textbook QuestionCardura, a drug used to treat hypertension, is synthesized as shown here. + K2CO3—> A KOH—> B HCl, H2O—> Cardura + CH3OH b. Show the mechanism for conversion of A to B. Which is formed more rapidly, A or B?441views
Textbook QuestionPropose a mechanism for the following reaction that explains why the configuration of the asymmetric center in the reactant is retained in the product: 389views
Textbook QuestionThe S_N2 reaction is the concerted, backside displacement of a good leaving group by a nucleophile [see Chapter 12]. Why do nucleophiles attack from the back in S_N2 reactions?250views
Textbook Question(••) For each pair, choose the haloalkane that would react most quickly in an Sₙ2 reaction.(a) <IMAGE> vs. <IMAGE>291views
Textbook Question(••) Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'(f) <IMAGE>279views
Textbook QuestionPractice your electron-pushing skills by drawing a mechanism for the following Sₙ2 reactions.(c) <IMAGE> 279views
Textbook Question(•) For each pair, choose the nucleophile that would react most quickly in an Sₙ2 reaction (assume H₂O is the solvent).(c) <IMAGE> vs. <IMAGE>269views
Textbook Question(••) For each pair, choose the haloalkane that would react most quickly in an Sₙ2 reaction.(c) <IMAGE> vs. <IMAGE>262views
Textbook QuestionIn which solvent—ethanol or diethyl ether—would the equilibrium for the following SN2 reaction lie farther to the right?<IMAGE>231views
Textbook QuestionHow will the rate of each of the following SN2 reactions change if it is carried out in a more polar solvent?b. <IMAGE>256views
Textbook QuestionHow will the rate of each of the following SN2 reactions change if it is carried out in a more polar solvent?c. CH3CH2I+NH3→CH3CH2N+H3 I−240views
Textbook QuestionShow all the products, including their configurations, that are obtained from the above reaction.244views
Textbook QuestionYou were told in [SECTION 7.11] that is best to use a methyl halide or a primary alkyl halide for the reaction of an acetylide ion with an alkyl halide. Explain why this is so.252views
Textbook QuestionWould you expect acetate ion (CH3CO2−) to be a better nucleophile in an SN2 reaction with an alkyl halide carried out in methanol or in dimethyl sulfoxide?298views
Textbook QuestionDraw a perspective structure or a Fischer projection for the products of the following SN2 reactions.e. <IMAGE> + NaOCH3 CH3OH—>308views
Textbook QuestionDraw a perspective structure or a Fischer projection for the products of the following SN2 reactions.f. <IMAGE> + NH3 excess 251views
Textbook QuestionPredict the compound in each pair that will undergo the SN2 reaction faster.(c) <IMAGE> or <IMAGE> (d) <IMAGE> or <IMAGE>236views
Textbook QuestionFor each pair of compounds, state which compound is the better SN2 substrate.c. 2-bromobutane or isopropyl bromided. 1-chloro-2,2-dimethylbutane or 2-chlorobutanee. 1-iodobutane or 2-iodopropane231views
Textbook QuestionTriethyloxonium tetrafluoroborate, (CH3CH2)3O+ BF4-, is a solid with melting point 91–92 °C. Show how this reagent can transfer an ethyl group to a nucleophile (Nuc:−) in an SN2 reaction. What is the leaving group? Why might this reagent be preferred to using an ethyl halide? (Consult [TABLE 6-2] <IMAGE>) 243views
Textbook Questionb. Explain why a much better yield of primary amine is obtained from the reaction of an alkyl halide with azide ion(-N3), followed by catalytic hydrogenation. (Hint: An alkyl azide is not nucleophilic.)<IMAGE>140views
Textbook QuestionConsider the reaction of 1-bromobutane with a large excess of ammonia (NH3). b. Draw the reactants, the transition state, and the products. Note that the initial product is the salt of an amine (RNH3+ Br−), which is deprotonated by the excess ammonia to give the amine.295views
Textbook QuestionDraw a perspective structure or a Fischer projection for the products of the following SN2 reactions.a. trans-1-bromo-3-methylcyclopentane + KOH b. (R)-2-bromopentane + KCN 255views
Textbook QuestionDraw a perspective structure or a Fischer projection for the products of the following SN2 reactions.c. <IMAGE> + NaI acetone—> d. <IMAGE> + NaSH 191views
Textbook QuestionPredict the major products of the following reactions.(d) the tosylate of cyclohexylmethanol + excess NH3(e) n-butyl tosylate + sodium acetylide, <IMAGE>239views
Textbook QuestionRank the following compounds in decreasing order of their reactivity toward the SN2 reaction with sodium ethoxide (Na+ -OCH2CH3) in ethanol.Methyl chlorideTert-butyl iodide Neopentyl bromideIsopropyl bromideMethyl iodideEthyl chloride249views
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.Why is no cis-2-bromobut-2-ene formed?3 bromobutan-2-ol <IMAGE> <IMAGE>trans-2-bromobut-2-ene <IMAGE>221views
Textbook Questiona. Explain why the alkyl halide shown here reacts much more rapidly with guanine than does a primary alkyl halide (such as pentyl chloride).<IMAGE>247views
Textbook QuestionUnder appropriate conditions, (S)-1-bromo-1-fluoroethane reacts with sodium methoxide to give pure (S)-1-fluoro-1-methoxyethane. CH3CHBrF (S) + NaOCH3 —> CH3CHFOCH3 (S) + NaBr a. Why is bromide rather than fluoride replaced? b. Draw perspective structures (as shown on the previous page for 2-bromobutane) for the starting material, the transition state, and the product. c. Does the product show retention or inversion of configuration? d. Is this result consistent with reaction by the SN2 mechanism?1070views
Textbook QuestionWhich of the following Sₙ2 reactions should proceed at a faster rate? Justify your answer on a reaction coordinate diagram.<IMAGE>vs.<IMAGE>246views
Textbook QuestionWrite the mechanism for the reaction of a cysteine side chain with iodoacetic acid.479views
Textbook QuestionAmines are good nucleophiles, even though they are neutral. How would the rate of an SN2 reaction between an amine and an alkyl halide be affected if the polarity of the solvent is increased?392views1rank
Textbook QuestionHow will the rate of each of the following SN2 reactions change if it is carried out in a more polar solvent? a. CH3CH2CH2CH2Br+HO− → CH3CH2CH2CH2OH+Br−389views
Textbook Question2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is stereospecific—that is, the stereoisomers obtained as products depend on the stereoisomer used as a reactant. Recall that because 2-acetoxycyclohexyl tosylate has two asymmetric centers, it has four stereoisomers—two are cis and two are trans. Explain the following observations: a. Both cis reactants form an optically active trans product, but each cis reactant forms a different trans product. 847views
Textbook Question2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is stereospecific—that is, the stereoisomers obtained as products depend on the stereoisomer used as a reactant. Recall that because 2-acetoxycyclohexyl tosylate has two asymmetric centers, it has four stereoisomers—two are cis and two are trans. Explain the following observations: c. A trans reactant is more reactive than a cis reactant. 351views
Textbook QuestionWhich substitution reaction takes place more rapidly? c. CH3CH2Cl + CH3O− or (in ethanol) CH3CH2Cl + CH3S−591views
Textbook QuestionWhat nucleophiles would form the following compounds as a result of reacting with 1-iodobutane? g. 340views
Textbook QuestionWhat nucleophiles would form the following compounds as a result of reacting with 1-iodobutane? h. 369views
Textbook QuestionStarting with an alkyl halide, how could the following compounds be prepared? a. 2-methoxybutane412views
Textbook QuestionStarting with an alkyl halide, how could the following compounds be prepared? b. 1-methoxybutane344views1rank
Textbook Question2-Acetoxycyclohexyl tosylate reacts with acetate ion to form 1,2-cyclohexanediol diacetate. The reaction is stereospecific—that is, the stereoisomers obtained as products depend on the stereoisomer used as a reactant. Recall that because 2-acetoxycyclohexyl tosylate has two asymmetric centers, it has four stereoisomers—two are cis and two are trans. Explain the following observations: b. Both trans reactants form the same racemic mixture. 364views
Textbook QuestionThe rate of the reaction of methyl iodide with quinuclidine was measured in nitrobenzene, and then the rate of the reaction of methyl iodide with triethylamine was measured in the same solvent. The concentration of the reagents was the same in both experiments. b. The same experiment was done using isopropyl iodide instead of methyl iodide. Which reaction had the larger rate constant?380views
Textbook QuestionThe rate of the reaction of methyl iodide with quinuclidine was measured in nitrobenzene, and then the rate of the reaction of methyl iodide with triethylamine was measured in the same solvent. The concentration of the reagents was the same in both experiments. c. Which alkyl halide has the larger kquinuclidine/ktriethylamine ratio? 525views
Textbook QuestionStarting with an alkyl halide, how could the following compounds be prepared? c. butylmethylamine336views
Textbook QuestionThe reaction of an amine with an alkyl halide gives an ammonium salt. R3N amine + R'—X alkyl halide —> R3(N+)—R' X- ammonium salt The rate of this SN2 reaction is sensitive to the polarity of the solvent. 1. Draw an energy diagram for this reaction in a nonpolar solvent and another in a polar solvent. 2. Consider the nature of the transition state, and explain why this reaction should be sensitive to the polarity of the solvent. 3. Predict whether it will be faster or slower in a more polar solvent.1439views
Textbook QuestionThe reaction of an amine with an alkyl halide gives an ammonium salt. R3N amine + R'—X alkyl halide —> R3(N+)—R' X- ammonium salt The rate of this SN2 reaction is sensitive to the polarity of the solvent. 1. Draw an energy diagram for this reaction in a nonpolar solvent and another in a polar solvent. 2. Consider the nature of the transition state, and explain why this reaction should be sensitive to the polarity of the solvent. 3. Predict whether it will be faster or slower in a more polar solvent.132views
Textbook QuestionUnder certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second. c. Show another SN2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces 1-methoxybutane.542views
Textbook QuestionShow how you might use SN2 reactions to convert 1-chlorobutane into the following compounds. c. 1-iodobutane d. CH3—(CH2)3—CN 885views
Textbook QuestionShow how you might use SN2 reactions to convert 1-chlorobutane into the following compounds. e. CH3—(CH2)3—C≡CH f. CH3CH2—O—(CH2)3—CH3 g. CH3—(CH2)3—NH2 585views
Textbook QuestionShow how each compound might be synthesized by the SN2 displacement of an alkyl halide. e. H2C=CH—CH2CN f. H—C≡C—CH2CH2CH31045views
Textbook QuestionGive two syntheses for (CH3)2CH—O—CH2CH3, and explain which synthesis is better.766views
Multiple Choice Which substrate will undergo a reaction with ethanol fastest at room temperature?294views
Multiple Choice For a 2nd order substitution reaction tripling the concentration of the substrate, R–X, and tripling the concentration of the nucleophile does what to the rate of the reaction?293views