Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 6, Problem 42DSP
Interpretation Introduction
Interpretation:
A compound that undergoes substitution by the
Concept Introduction:
In general,
Primary alkyl halides are less crowded at the site of substitution than secondary and tertiary alkyl halides and thus react faster in substitution by
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OH
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H3C
CH3
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Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are
measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the
reaction is first order. The substitution reaction is thus termed Sy1, and the elimination reaction is termed E1. These
reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving
group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or
elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to
either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1
elimination follows Zaitsev's rule and typically yields the most substituted alkene as the major product.
Conditions which favor the Sy1/E1 pathway include…
The following reaction gives a mixture of the nucleophilic substitution (SN1 or SN2) and elimination (E1 or E2) products. Propose two mechanisms that can account for the formation of these products. One mechanism should be for the nucleophilic substitution reaction and the other mechanism would show the elimination reaction.
The reaction of methylpropene with HBr, under radical conditions, gives two
intermediates. Propose a mechanism for the formation of the two products.
Propose a mechanism for the following reaction and use electronic factors to account for
the formation of a major product:
CH2
CH2Br
N-Bromosuccinimide (NBS)
ho, CCI4
Draw the structure of an antioxidant, Vitamin E free radical and use resonance structures
o account for its stability.
Chapter 6 Solutions
Organic Chemistry - Standalone book
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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- b) 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_forwardIn SN2 reactions of haloalkanes, the order of reactivity is RI>RBr>RCl>RF. Alkyl iodides are considerably more reactive than alkyl fluorides, often by factors as great as 106. All 1-halo-2,4-dinitrobenzenes, however, react at approximately the same rate in nucleophilic aromatic substitutions. Account for this difference in relative reactivities.arrow_forward8A In the following compounds indicate with an arrow or arrows the position or positions in aromatic ring which will undergo an electrophilic aromatic reaction substitution. Justify your answer (i) NC. OCH 3 (il) Oarrow_forward
- 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.Which compound undergoes substitution by the SN2 mechanism at the fastest rate?arrow_forwardIn the chemical reaction between bromocyclopentane 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.arrow_forwardConsider the compound below, with all its carbons labeled. In reality we might predict that the alkene groups are more reactive to electrophiles, but instead imagine that an electrophile binds to carbon five as the first step of an electrophilic aromatic substitution mechanism. A carbocation results, with multiple resonance structures. Select every carbon that bears a positive charge in one of these resonance structures. 10 Carbon 1 O Carbon 2 Carbon 3 OCarbon 4 OCarbon 5 OCarbon 6 Carbon 7 Carbon 8 Carbon 9 Oerboi 10.arrow_forward
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