EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
3rd Edition
ISBN: 9780133858501
Author: Bruice
Publisher: PEARSON CO
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Textbook Question
Chapter 9.2, Problem 4P
Why are NH3 and CH3NH2 no longer nucleophiles when they are protonated?
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4.
A CHEM 245 student wants to synthesize some ethylene glycol to use as antifreeze in his
radiator this winter. He proposes the following reaction to his instructor, who quickly explains that this
reaction won't work as proposed due to the student's choice of reagent.
1) NaH
2) H20
OH
Но
a) Why can't sodium hydride (NaH) be used as the nucleophile in the reaction above?
b) Propose an alternate reagent that COULD be used with the ethylene oxide to successfully give the
desired ethylene glycol product.
7.
These are all electron-withdrawing groups that slow electrophilic aromatic substitution, with one exception. Which one?
© CO,H
O NO₂
O CF3
O NH2
Chapter 9 Solutions
EP ESSENTIAL ORG.CHEM.-MOD.MASTERING
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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- Explain why the following reaction sequence will not occur: NH2 NH2 HNO3 H2SO4 O2Narrow_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_forward10:54 ← Question 21 of 32 Draw the major product of this reaction. Ignore inorganic byproducts. Submit Assume that the water side product is continuously removed to drive the reaction toward products. (CH3)2NH, TSOH Select to Draw | I Iarrow_forward
- Which of the following species are likely to be nucleophiles and which electrophiles? Wich might be both?arrow_forwardConsider the following SN1 reaction: (CH3)3CBR + H2O → (CH3)3COH + HBr What is the effect of doubling both the t-butyl bromide and water concentrations on the rate of the reaction? O doubles the rate O quadruples the rate O triples the rate O halves the rate O no change O quarters the rate O 1/16th the ratearrow_forwardAn electrostatic potential map of boron trifluoride is shown. Is BF3 likely to be a ucleophile or an electrophile? Draw a Lewis structure for BF3, and explain your answer. BF3arrow_forward
- When trichloroacetaldehyde is dissolved in water, almost all of it is converted to the hydrate. Chloral hydrate, the product of the reaction, is a sedative that can be lethal. A cocktail laced with it is known—in detective novels, at least—as a “Mickey Finn.” Explain why an aqueous solution of trichloroacetaldehyde is almost all hydrate.arrow_forwardPlease don't provide handwrittin solution....arrow_forwardIn both examples below the reactants shown are combined to bring about a nucleophilic substitution (Sy1, Sy2) and/or elimination (E1, E2) reaction. What is the major reaction that takes place in each case? CI CH2CI NaOH H20 SN2 E2 mixture of SN1 and E1 CH3 CI CH3OH CH3arrow_forward
- Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution. bl || A. B. C. D. E. NH₂ مل I > IV > III > || || > ||| > IV >| | > ||| > || > IV III > IV> || > | IV > I > III > || IVarrow_forwardComplete the following reactions: indicate the mechanism (SN1 or SN2). If the reaction does not proceed, indicate so and the reason as to why it would not.arrow_forwardb) Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OMe HO + OMe + OH HO + CH; OHarrow_forward
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