EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 10.1, Problem 1P
Why are NH3 and CH3NH2 no longer nucleophiles when they are protonated?
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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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- 2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff' for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH₂OHarrow_forwardHCOO- > HO- > (CH3)2 Sort from best nucleophile to worst nucleophilearrow_forwardChoose all the nucleophiles OH- H3O+ NH4+ CH3OH (CH3)3CLi CH3CH2CH3 NaNH2 CH3SNaarrow_forward
- which of the following alkenes will most likely undergo a hydride shift when reacting with HCl?arrow_forwardThese are all electron-withdrawing groups that slow electrophilic aromatic substitution, with one exception. Which one? © CO,H O NO₂ O CF3 O NH2arrow_forwardWhich one of the following molecules CANNOT undergo a nucleophilic aromatic substitution reaction? o O2N. O,N `NO2 NO2 F NO2 NO2 NO2 NO2 `NO2 NO2 Brarrow_forward
- 9. Which of the following nucleophiles can undergo a substitution reaction with an alcohol under strongly acidic conditions? NH₂ - A B Br C D MgBrarrow_forwardWhich of the following species is likely to be a nucleophile and which an electrophile? (a) CH3CI {b) CH3S (c) N CH3 {d) N. CH3CHarrow_forwardList the following in increasing order of nucleophilic strength. CH3COO-, H2O, CH3O-, OH-, CH3CH20-arrow_forward
- Explain why quinuclidine is a much more reactive nucleophile thantriethylamine, even though both compounds have N atoms surroundedby three R groups.arrow_forwardH3C-C O: H ethanal :CN: and the electrophile is cyanide ion In the step you have just written, the nucleophile is slow rate-determining Ö—0—1 H3C-C-C=N; adductarrow_forward.Which one of the following molecules can react as electrophile in reactions with alkenes? CH3OH NaCI HCI KCN NaCI O HCI O KCN O CH3OHarrow_forward
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