EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 10, Problem 62P
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What alkenes would you expect to be obtained from the acid-catalyzed dehydration of 1-hexanol?
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Draw structural formulas for the alkenes formed by acid-catalyzed dehydration of each alcohol. Where isomeric alkenes are possible, predict which is the major product.
Q.) 1-Methylcyclopentanol
Chapter 10 Solutions
EBK ORGANIC CHEMISTRY
Ch. 10.1 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 10.1 - Explain the difference in reactivity between...Ch. 10.1 - Prob. 5PCh. 10.1 - Prob. 6PCh. 10.1 - Prob. 8PCh. 10.2 - Prob. 9PCh. 10.3 - Prob. 11PCh. 10.3 - Show how 1-propanol can be converted into the...Ch. 10.4 - Which of the following alcohols dehydrates the...Ch. 10.4 - Prob. 14P
Ch. 10.4 - Prob. 15PCh. 10.4 - Propose a mechanism for each of the following...Ch. 10.4 - Draw the product of each of the following...Ch. 10.4 - Explain why the following alcohols, when heated...Ch. 10.4 - What stereoisomers are formed in the following...Ch. 10.4 - Prob. 20PCh. 10.4 - What alcohol would you treat with phosphorus...Ch. 10.5 - Prob. 22PCh. 10.6 - What are the major products obtained when each of...Ch. 10.6 - Prob. 26PCh. 10.7 - Prob. 27PCh. 10.7 - Would you expect the reactivity of a five-membered...Ch. 10.7 - Prob. 29PCh. 10.7 - What products are obtained from the reaction of...Ch. 10.7 - Prob. 31PCh. 10.7 - Prob. 32PCh. 10.7 - Prob. 33PCh. 10.8 - Draw the mechanism for formation of the two...Ch. 10.8 - Prob. 35PCh. 10.8 - Prob. 36PCh. 10.8 - How do the major products obtained from...Ch. 10.8 - Explain why the two arene oxides in Problem 38...Ch. 10.8 - Which compound is more likely to be carcinogenic?Ch. 10.8 - Three arene oxides can be obtained from...Ch. 10.9 - Explain why the half-life (the time it takes for...Ch. 10.10 - Prob. 43PCh. 10.10 - Prob. 44PCh. 10.10 - Prob. 45PCh. 10.10 - Prob. 46PCh. 10.10 - Prob. 47PCh. 10.10 - Describe a synthesis for each of the following...Ch. 10.11 - Using an alkyl halide and a thiol as starting...Ch. 10.11 - The following three nitrogen mustards were studied...Ch. 10.11 - Why is melphalan a good cancer drug?Ch. 10.11 - Prob. 53PCh. 10.12 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 55PCh. 10 - Which compound is more likely to be carcinogenic?Ch. 10 - Prob. 57PCh. 10 - Prob. 58PCh. 10 - When heated with H2SO4, both...Ch. 10 - What is the major product obtained from the...Ch. 10 - Write the appropriate reagent over each arrow.Ch. 10 - What alkenes would you expect to be obtained from...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - When deuterated phenanthrene oxide undergoes a...Ch. 10 - An unknown alcohol with a molecular formula of...Ch. 10 - Explain why the acid-catalyzed dehydration of an...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - What product would be formed if the four-membered...Ch. 10 - Which of the following ethers would be obtained in...Ch. 10 - Using the given starting material any necessary...Ch. 10 - Prob. 74PCh. 10 - When 3-methyl-2-butanol is heated with...Ch. 10 - Draw structures for compounds AF.Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - How could you synthesize isopropyl propyl ether,...Ch. 10 - When ethyl ether is heated with excess HI for...Ch. 10 - When the following seven-membered ring alcohol is...Ch. 10 - Ethylene oxide reacts readily with HO because of...Ch. 10 - Describe how each of the following compounds could...Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - Triethylene glycol is one of the products obtained...Ch. 10 - Prob. 85PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 87PCh. 10 - An ion with a positively charged nitrogen atom in...Ch. 10 - The following reaction takes place several times...Ch. 10 - Prob. 90PCh. 10 - Propose a mechanism for each of the following...Ch. 10 - A vicinal diol has OH groups on adjacent carbons....Ch. 10 - Prob. 93PCh. 10 - Prob. 94PCh. 10 - Two stereoisomers are obtained from the reaction...Ch. 10 - Propose a mechanism for each or the following...Ch. 10 - Triethylenemelamine (TEM) is an antitumor agent....
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- 4.) HX is used as a reagent in the reaction below. „NH2 он + HX + :NEN: + A. What functional-group transformation occurs in this reaction?arrow_forwardGive the systematic (IUPAC) names for these molecules. Boononon cnolonongron. НаСНз CHОССH2СH2СНCHЗ CH3 phenyl propanoate |4-methyl pentane methanoat Incorrect. You mixed up the acyl and alkoxy portions of the molecule. Name the alkoxy part first, followed by the acyl part.arrow_forwardAcid-catalyzed dehydration of 3-methyl-2-pentanol gives three alkenes: 3-methyl-1-pentene, 3-methyl-2-pentene, and 3-methylenepentane. Draw the structure of the carbocation intermediate leading to the formation of 3-methyl-2-pentene.arrow_forward
- Write in the correct reagents for these transformations: a) cyclohexanol -→ chlorocyclohexane b) 2-butanone 2-butanol ward 2-butanol 2-butanone toluene - → benzoic acid nitrobenzene → anilinearrow_forwardRank the following alcohols in order of increasing ease of acid-catalyzed dehydration. Provide the structure of the dehydration product (alkene) from each alcohol. OH OH 3 1 a OHarrow_forwardDraw the overall reaction of 1-butanol with HBr and H2SO4 to form 1-bromobutane.arrow_forward
- 0 CH₂ → ?? If the above compound is subjected to combustion, what are the products? ethanoic acid +2-phenyl-ethene-1-ol 15CO₂ (g) + 5H₂0 (g) O 2-phenyl-ethyl-ethanoate + H₂O 20CO₂ (g) + 10H₂O(g) →?? CH, if the above compound was treated with H and H₂O what product will form?arrow_forwardDraw the structure of the chlorohydrin formed by treating 1-methylcyclohexene with Cl2/H2O.arrow_forwardSelect the reagent that you would use to convert an alkene to a Markovnikov (more substituted) alcohol without possibility of carbocation rearrangement. o H2SO4, H2O OBH3-THF, then H2O2, H2O, NaOH Hg(OAc)2, H2O, then NaBH4 o OsO4, TBHP, H2Oarrow_forward
- 10) For the reaction between isopropyl 1-propyl (or 'n-propyl') ether and HBr, which type of reaction best matches the expected products? A) Acid-catalyzed dehydration B) Nucleophilic substitution reaction C) Ether cleavage reaction D) Nucleophilic addition-elimination reactionarrow_forwardComplete these syntheses.arrow_forwardAcid-catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The first step is the protonation of the alcohol oxygen to form an oxonium ion. Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures, including hydrogen atoms, of the three organic products of this reaction. н н :бн н Нас. Нас. CHз CH3 ČH3 CH3 3-methyl-2-butanol an oxonium ion Major Product Minor Product Minor Productarrow_forward
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