Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 6, Problem 35P
Based on what we know about nucleophiles and leaving groups, we suspect that the reaction of
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what would a detailed step-by-step mechanism be for a reaction between bromine and trans-stilbene if the solvent, ethanol, is a stronger nucleophile than the bromide ions?
why do (R)-3-chloro-1-methylcycloprop-1-ene and 5-Bromo-1,3-Cyclohexadiene react differently with cyanide (why doesn't cyanide pass through its usual mechanism for these two products and what did you obtain these specific products)
7. For each pair of compounds, say which compound is the best SN2 substrate.(a) 2-methyl-1-iodopropane or tert-butyl iodide(b) cyclohexyl bromide or 1-bromo-1-methylcyclohexane(c) 2-bromobutane or isopropyl bromide(d) 1-chloro-2,2-dimethylbutane or 2-chlorobutane(e) 1-iodobutane or 2-iodopropane
Chapter 6 Solutions
Organic Chemistry - Standalone book
Ch. 6.1 - Prob. 1PCh. 6.2 - 1-Bromo-3-chloropropane reacts with one molar...Ch. 6.3 - Prob. 3PCh. 6.3 - The Fischer projection for (+)-2-bromooctane is...Ch. 6.3 - Would you expect the 2-octanol formed by SN2...Ch. 6.3 - Prob. 6PCh. 6.4 - Prob. 7PCh. 6.4 - The first step in the synthesis of the...Ch. 6.6 - Prob. 9PCh. 6.6 - Prob. 10P
Ch. 6.7 - Prob. 11PCh. 6.8 - Prob. 12PCh. 6.9 - Diethyl ether (CH3CH2OCH2CH3) has a dielectric...Ch. 6.9 - Unlike protic solvent which solvate from complexes...Ch. 6.10 - Prob. 15PCh. 6.10 - Prob. 16PCh. 6.10 - The hydrolysis of sulfonate of 2-octanol is...Ch. 6.11 - Prob. 18PCh. 6 - Prob. 19PCh. 6 - Prob. 20PCh. 6 - Both of the following reactions involve...Ch. 6 - Prob. 22PCh. 6 - Prob. 23PCh. 6 - Sodium nitrite (NaNO2) reacted with 2-iodooctane...Ch. 6 - Prob. 25PCh. 6 - Prob. 26PCh. 6 - Prob. 27PCh. 6 - The reaction of 2,2-dimethyl-1-propanol with HBr...Ch. 6 - If the temperature is not kept below 25oC during...Ch. 6 - The reaction of cyclopentyl bromide with sodium...Ch. 6 - Prob. 31PCh. 6 - Prob. 32PCh. 6 - Write an equation, clearly showing the...Ch. 6 - Prob. 34PCh. 6 - Based on what we know about nucleophiles and...Ch. 6 - Prob. 36PCh. 6 - Prob. 37PCh. 6 - Prob. 38PCh. 6 - Prob. 39PCh. 6 - Prob. 40PCh. 6 - Prob. 41DSPCh. 6 - Prob. 42DSPCh. 6 - Prob. 43DSPCh. 6 - Prob. 44DSPCh. 6 - Prob. 45DSPCh. 6 - Prob. 46DSP
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- (a) The reaction of (R)-2-bromopentane with NaOH in ethanol produced a racemic mixture. 3. Br Ho.. NaOH Ethanol Racemic mixture (i) Draw the structures of the products indicating stereochemistry (b) For the reaction in part (a) above describe the effect of each of the following changes on the outcome of the reaction. Provide clear explanations for your answers. (i) The concentration of the nucleophile is doubled. (ii) The solvent is changed from ethanol to dimethyl sulfoxide (DMSO)arrow_forwardin a reaction where trans-stilbene reacts with a molecule of bromine while using ethanol as a solvent, what would happen if the ethanol was a more reactive nucleophile than the bromide ion(s)? would the product be affected?arrow_forwardFollowing compounds are given to you:2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane(i) Write the compound which is most reactive towards SN2 reaction.(ii) Write the compound which is optically active.(iii) Write the compound which is most reactive towards β – elimination reactionarrow_forward
- Which product would be obtained if 3-methyl-2-butanol was used as the alcohol in the Electrophilic Aromatic Substitution: Friedel-Crafts Alkylation? Show the structure of the product. Explain briefly. Original reaction and more info is attached:arrow_forward5) Draw the product of the reaction of (S)-pentan-2-ol with (a) SOCI₂ in diethyl ether (b) Dess-Martin Periodinane in CH₂Cl2 6) Draw the product of the reaction of 4-methylpentanoic acid with (a) (1) NaBH4, ethanol (2) H3O+ (b) (1) LiAlH4, ether (2) H3O+arrow_forwardWhich alkyl halide in each of the following pairs will react faster in an SN2 reaction with OH? Explain your answer briefly. (a) Bromobenzene or benzyl bromide, C6H5CH2B. (b) CH3C1 or (CH3)3CCI (c) CH3CH=CHBr or H2C=CHCH2BRarrow_forward
- What would be the product of a reaction involving 2-methyl-2-pentene and HBr both with and without the presence of peroxides?arrow_forwardIn the electrophilic aromatic substitution of toluene formation of 4-chlorotoluene is favored over 3-chlorotoluene. Explain this observation by writing the reaction mechanism.?arrow_forwardProvide the reagents necessary to convert (R)-2-chlorobutane to (S)-2-methoxybutane.arrow_forward
- Using the pKa values of the conjugate acids of the leaving groups (the pKa of HBr is -9, and the pKa of H2O is 15.7), explain the difference in reactivity between CH3Br and CH3OH in a nucleophilic substitution reaction.arrow_forwardThe base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.arrow_forwardWhat reaction presented in this chapter is occurring in the following equation? Explain the resulting stereochemistry of the reaction.arrow_forward
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