Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 11.7, Problem 25P
Would you expect the reactivity of a five-membered ring ether such as tetrahydrofuran (Table 10.2) to be more similar to the reactivity of an
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Chapter 11 Solutions
Organic Chemistry
Ch. 11.1 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 11.1 - Prob. 2PCh. 11.1 - Prob. 5PCh. 11.2 - Prob. 7PCh. 11.3 - Prob. 9PCh. 11.3 - Show how 1-propanol can be converted into the...Ch. 11.4 - Which of the following alcohols dehydrates the...Ch. 11.4 - Prob. 12PCh. 11.4 - Prob. 13PCh. 11.4 - Propose a mechanism for each of the following...
Ch. 11.4 - Draw the product of each of the following...Ch. 11.4 - Explain why the following alcohols, when heated...Ch. 11.4 - What stereoisomers are formed in the following...Ch. 11.4 - Prob. 18PCh. 11.4 - What alcohol would you treat with phosphorus...Ch. 11.5 - Prob. 20PCh. 11.6 - Prob. 22PCh. 11.7 - Prob. 24PCh. 11.7 - Would you expect the reactivity of a five-membered...Ch. 11.7 - Prob. 26PCh. 11.7 - What products are obtained from the reaction of...Ch. 11.7 - Prob. 28PCh. 11.7 - Prob. 29PCh. 11.7 - Prob. 30PCh. 11.8 - Prob. 31PCh. 11.8 - Prob. 32PCh. 11.8 - How do the major products obtained from...Ch. 11.8 - Explain why the two arene oxides in Problem 38...Ch. 11.8 - Three arene oxides can be obtained from...Ch. 11.9 - Explain why the half-life (the time it takes for...Ch. 11.10 - Prob. 38PCh. 11.10 - Prob. 39PCh. 11.10 - Prob. 40PCh. 11.10 - Prob. 41PCh. 11.10 - Prob. 42PCh. 11.11 - Using an alkyl halide and a thiol as starting...Ch. 11.11 - The following three nitrogen mustards were studied...Ch. 11.11 - Why is melphalan a good cancer drug?Ch. 11.11 - Prob. 47PCh. 11 - Prob. 48PCh. 11 - Which compound is more likely to be carcinogenic?Ch. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Write the appropriate reagent over each arrow.Ch. 11 - What alkenes would you expect to be obtained from...Ch. 11 - Prob. 54PCh. 11 - When heated with H2SO4, both...Ch. 11 - What is the major product obtained from the...Ch. 11 - When deuterated phenanthrene oxide undergoes a...Ch. 11 - An unknown alcohol with a molecular formula of...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Propose a mechanism for the following reaction:Ch. 11 - What product would be formed if the four-membered...Ch. 11 - Which of the following ethers would be obtained in...Ch. 11 - Using the given starting material any necessary...Ch. 11 - Prob. 65PCh. 11 - When 3-methyl-2-butanol is heated with...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - How could you synthesize isopropyl propyl ether,...Ch. 11 - When the following seven-membered ring alcohol is...Ch. 11 - Ethylene oxide reacts readily with HO because of...Ch. 11 - Prob. 71PCh. 11 - Propose a mechanism for each of the following...Ch. 11 - Explain why the acid-catalyzed dehydration of an...Ch. 11 - Triethylene glycol is one of the products obtained...Ch. 11 - Prob. 75PCh. 11 - Prob. 76PCh. 11 - When ethyl ether is heated with excess HI for...Ch. 11 - Propose a mechanism for the following reaction:Ch. 11 - Prob. 79PCh. 11 - An ion with a positively charged nitrogen atom in...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - Prob. 82PCh. 11 - The following reaction takes place several times...Ch. 11 - A vicinal diol has OH groups on adjacent carbons....Ch. 11 - Prob. 85PCh. 11 - Prob. 86PCh. 11 - Two stereoisomers are obtained from the reaction...Ch. 11 - Propose a mechanism for each or the following...Ch. 11 - Triethylenemelamine (TEM) is an antitumor agent....
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- Explain why the C=C of an enol is more nucleophilic than the C=C of an alkene, despite the fact that the electronegative oxygen atom of the enol inductively withdraws electron density from the carbon–carbon double bond.arrow_forwardWrite the structures of all the constitutionally isomeric ethers of molecular formula C5H12O, and give an acceptable name for each.arrow_forwardDraw the structural formula of the enol formed in each alkyne hydration reaction; then draw the structural formula of the carbonyl compound with which each enol is in equilibriumarrow_forward
- Cyclopropenones are described as having aromatic character. How would you account for this, given that the ring contains three ℼ-electronarrow_forwardThe structure below is the cyclic ether (epoxide), butene oxide: (1) CH3CH₂ -CH₂ butene oxide How could this compound be prepared from but-1-ene? Explain why butene oxide is much more reactive than its isomer, tetrahydrofuran, which is also a cyclic ether: H₂C-CH₂ H₂C CH₂ tetrahydrofuran Illustrate how butene oxide reacts with ammonia, showing details of the mechanism leading to the final product, C4H11 NO.arrow_forward5) Compound A reacted with Mg in ether to give B. Compound B is with Ethyl bromide to give Ethyl cyclohexane. What are the structures of A and B?arrow_forward
- 4. A certain endothermic reaction X carried out room temperature (273K) has an enthalpy change of 20 Kcal/mol and an entropy change of 10 Kcal/K/mol. i) Calculate the Gibbs free energy (AG) of this reaction. ii) Is this reaction spontaneous or non-spontaneous? Give a reason for your answer 5. Thiomethane reacts with compound A via an SN1 reaction. Complete its reaction equation below. ii) SH Compound A ii) Draw the mechanism of reaction for this reaction. 6. Butyl Chloride undergoes an elimination reaction when reacted with sodium ethoxide to form butene. The reaction equation is given below with two reaction products A and B. low inevloa CI noitsups p *OEt B Which is the major product, and which is minor product. (Hint: Look up how the size of the base affects the elimination reaction product) Give a reason for your answer.arrow_forwardZaitsev's rule for the acid catalyzed dehydration of alcohols states: It states that in a regioselective E1 or E2 reaction the major product is the least stable alkene, i.e., the alkene with the less substituted double bond. O 1) True O 2) Falsearrow_forwardHw.184. Provide the major organic product in the reaction below: 1) Methyl-1,2-cyclopentene oxide addition of HBrarrow_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_forwardCompound A and compound B are in equilibrium. Write a stepwise mechanism from compound Ato compound B showing ALL intermediates. Use curved arrows to symbolize the flow of electrons to show how each of the intermediates and products are formed. Show all lone pairs and formal charges. Lastly, explain which compound (Aor B) will be in higher concentration.arrow_forwardAccount for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.arrow_forward
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