Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 9, Problem 54P
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In the acid catalyzed dehydration of 2,2-dimethyl-1-cyclohexanol, draw all possible alkenes, including those resulting from rearrangement.
Give the IUPAC name of the product that would form when the following alkene undergoes catalytic hydrogenation.
CH,
CH=CHCHCH,
Name of product
!3!
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 9 Solutions
Essential Organic Chemistry, Global Edition
Ch. 9.1 - Draw the structures of straight-chain alcohols...Ch. 9.1 - Prob. 2PCh. 9.1 - Prob. 3PCh. 9.2 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 9.2 - Prob. 5PCh. 9.2 - The observed relative reactivities of primary,...Ch. 9.4 - Which of the following alcohols would dehydrate...Ch. 9.4 - Prob. 10PCh. 9.4 - Prob. 11PCh. 9.4 - Prob. 12P
Ch. 9.4 - Prob. 13PCh. 9.5 - What product will be obtained from the reaction of...Ch. 9.5 - Prob. 15PCh. 9.6 - a. What is each ethers systematic name? 1....Ch. 9.8 - Draw the structure of the following: a....Ch. 9.8 - Prob. 20PCh. 9.8 - Would you expect the reactivity of a five-membered...Ch. 9.9 - Explain why the two arene oxides in Problem 22...Ch. 9.9 - Which compound is more likely to be...Ch. 9.11 - The following three nitrogen mustards were studied...Ch. 9 - What are the common and systematic names of the...Ch. 9 - Prob. 28PCh. 9 - Prob. 29PCh. 9 - Prob. 30PCh. 9 - Prob. 31PCh. 9 - What is the major product obtained from the...Ch. 9 - Draw structures for the following: a....Ch. 9 - Prob. 34PCh. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Prob. 37PCh. 9 - Ethylene oxide reacts readily with HO.because of...Ch. 9 - Propose a mechanism for each of the following...Ch. 9 - Which of the following ethers would be obtained in...Ch. 9 - Show how each of the following syntheses could be...Ch. 9 - Prob. 42PCh. 9 - Prob. 43PCh. 9 - Prob. 44PCh. 9 - Propose a mechanism for each of the following...Ch. 9 - a. Propose a mechanism for the following reaction:...Ch. 9 - Three arene oxides can be obtained from...Ch. 9 - Prob. 48PCh. 9 - The following reaction takes place several times...Ch. 9 - Show how each of the following compounds could be...Ch. 9 - Propose a mechanism for the following reaction:Ch. 9 - Propose a mechanism for the following reaction:Ch. 9 - What alkenes would you expect to be obtained from...Ch. 9 - Triethylenemelamine (TEM) is an antitumor agent....Ch. 9 - When a diol that has OH groups on adjacent carbons...Ch. 9 - What product is obtained when...Ch. 9 - Prob. 58P
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- Synthesize 4-octanol using only 1-butene as your source of carbonarrow_forwardWhat are the three alkenes formed in the acid-catalyzed dehydration of 2-pentanol? Propose the mechanism of their formation.arrow_forwardAcid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl- 1-butene, and 2,3-dimethyl-1-butene. Draw the structure of the carbocation intermediate leading to the formation of 2,3-dimethyl-2-butene. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • If more than one structure fits the description, draw them all. • Separate structures with + signs from the drop-down menu. / H₂C CH₂ CH3 CH3 ChemDoodleⓇ On []arrow_forward
- Give 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 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl-1-butene, and 2,3-dimethyl-1- butene. Draw the structure of the carbocation intermediate leading to the formation of 2,3-dimethyl-2-butene. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. If more than one structure fits the description, draw them all. Separate structures with + signs from the drop-down menu. C P opy aste ChemDoodle >arrow_forwardWhat reaction conditions are needed to convert (R)-2-ethyl-2- methyloxirane to (R)-2-methylbutane-1,2-diol ?arrow_forward
- 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_forwardWrite 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_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
- Rank 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_forward0 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_forward
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