EBK ORGANIC CHEMISTRY
10th Edition
ISBN: 9781259636875
Author: Carey
Publisher: MCGRAW HILL BOOK COMPANY
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Question
Chapter 6, Problem 46DSP
Interpretation Introduction
Interpretation:
The equation including the curved arrows that best represents the rate determining step in the mechanism is to written.
Concept Introduction:
The slowest step in the substitution reaction is the rate determining step.
For the substitution reactions by an
Thus,
Curved arrows indicate the movement of electrons in a mechanism.
Primary carbocations are not stable and so, they do not form as a carbocation intermediate in a given mechanism.
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1.
In which of the following tests/reagents would cyclohexene and hexane both yield a positive result?
I. t-BuCl in AlCl3
II. Br2 in light
III. Halogenation by I2 in KI
IV. KMnO4
2.
Which of the following is statements is/are TRUE about the experiment on the relative rates of electrophilic aromatic substitution?I. The experiment must be performed in dark conditions.
II. Using the same solvents, a faster decolorization will be observed in aniline as compared to ethylbenzene.
III. Chlorobenzene will react faster than methoxybenzene.
IV. The use of AlCl3 in the halogenation of aromatic compounds using elemental bromine could hasten the reaction.
These problems differ from those in earlier chapters in that they directly test your knowledge of core material rather than using a descriptive passage to extend the material or introduce new ideas. The number of factors that contribute to nucleophilic substitution can be daunting. The really major ones, though, are few and readily applied to specific reactions by using the SN1 and SN2 mechanisms to guide your analysis.What is the major product of the reaction shown?
In the chemical reaction between 2-chloro-2-methyl-propane and ethanolic silver nitrate solution, a precipitate is definitely formed. Using the skeletal structures of the molecules, write out the skeletal structure of each reaction (don't include the mechanism). Identify what the nucleophile is in each type of reaction, especially within this SN1 reaction. Explain the reactivity of each electrophile/substrate in terms of whether they are tertiary, secondary, primary, etc. for each reaction. Include the overall chemical reaction.
Chapter 6 Solutions
EBK ORGANIC CHEMISTRY
Ch. 6.1 - Prob. 1PCh. 6.2 - 1-Bromo-3-chloropropane reacts with one molar...Ch. 6.3 - Prob. 3PCh. 6.3 - The Fischer projection for (+)-2-bromooctane is...Ch. 6.3 - Would you expect the 2-octanol formed by SN2...Ch. 6.3 - Prob. 6PCh. 6.4 - Prob. 7PCh. 6.4 - The first step in the synthesis of the...Ch. 6.6 - Prob. 9PCh. 6.6 - Prob. 10P
Ch. 6.7 - Prob. 11PCh. 6.8 - Prob. 12PCh. 6.9 - Diethyl ether (CH3CH2OCH2CH3) has a dielectric...Ch. 6.9 - Unlike protic solvent which solvate from complexes...Ch. 6.10 - Prob. 15PCh. 6.10 - Prob. 16PCh. 6.10 - The hydrolysis of sulfonate of 2-octanol is...Ch. 6.11 - Prob. 18PCh. 6 - Prob. 19PCh. 6 - Prob. 20PCh. 6 - Both of the following reactions involve...Ch. 6 - Prob. 22PCh. 6 - Prob. 23PCh. 6 - Sodium nitrite (NaNO2) reacted with 2-iodooctane...Ch. 6 - Prob. 25PCh. 6 - Prob. 26PCh. 6 - Prob. 27PCh. 6 - The reaction of 2,2-dimethyl-1-propanol with HBr...Ch. 6 - If the temperature is not kept below 25oC during...Ch. 6 - The reaction of cyclopentyl bromide with sodium...Ch. 6 - Prob. 31PCh. 6 - Prob. 32PCh. 6 - Write an equation, clearly showing the...Ch. 6 - Prob. 34PCh. 6 - Based on what we know about nucleophiles and...Ch. 6 - Prob. 36PCh. 6 - Prob. 37PCh. 6 - Prob. 38PCh. 6 - Prob. 39PCh. 6 - Prob. 40PCh. 6 - Prob. 41DSPCh. 6 - Prob. 42DSPCh. 6 - Prob. 43DSPCh. 6 - Prob. 44DSPCh. 6 - Prob. 45DSPCh. 6 - Prob. 46DSP
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- State the characteristic of the SN2 and SN1 mechanism towards alkyl halide compounds based onmolecularity, reaction rate constant, formation of product(s), reactivity of alkyl halides and thestrength of nucleophile.arrow_forwardwe know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?arrow_forwardIn the chemical reaction between 1-Bromobutane and ethanolic silver nitrate solution, a precipitate is barely formed. Using the skeletal structures of the molecules, write out the skeletal structure of each reaction (don't include the mechanism). Identify what the nucleophile is in each type of reaction, especially the SN1 reaction. Explain the reactivity of each electrophile/substrate in terms of whether they are tertiary, secondary, primary, etc. for each reaction. Include the overall chemical reaction.arrow_forward
- Understanding different substitution and elimination pathways gives useful insight into chemical mechanisms and pathways. Give the different important aspects of the Sn1, Sn2, E1, E2, and E2cB reactions.arrow_forwardThe reaction of 1-iodopropane with potassium thiocyanate (KSCN) in certain solvents results in the formation of two isomeric products, propylthiocyanate and propylisothiocyanate (see scheme below), via the SN2 reaction mechanism. Attempts to prepare a similar mixture of these same isomeric products (propylthiocyanate and propylisothiocyanate) starting from 1-propene is illustrated below. Despite the strong acidity of thiocyanic acid (recall pKa = 1.1), this addition reaction does not lead to either of the products indicated. Based on your knowledge of alkene addition reactions, explain this experimental result.arrow_forwardCan you answer this question regarding this procedure: Discuss the Sn1 mechanism and then summarize how the different conditions impacted the rate. Look at leaving group, solvent, and substitution. What trends did you observe? Did any of the results turn out differently than you had expected? Do you think this is because of the mechanism or because of practical issues? Suggest possible ways to improve on the rate study for future trials.arrow_forward
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