Experimental Organic Chemistry: A Miniscale & Microscale Approach (Cengage Learning Laboratory Series for Organic Chemistry)
6th Edition
ISBN: 9781305080461
Author: John C. Gilbert, Stephen F. Martin
Publisher: Brooks Cole
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Chapter 9.3, Problem 8E
Interpretation Introduction
Interpretation: In the free-radical chain bromination reaction, the six given hydrocarbons should be arranged in increasing order.
Concept introduction:
Free radicals are uncharged molecules having an unpaired valence electron.
These are typically highly reactive and short-lived molecules.
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b) Explain in detail what characteristics of the alkyl halide influence whether a
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will be SN1 or SN2.
A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a) Draw the resonance forms of the three possible allylic free radical intermediates.
What is the arrangement between the structures in the order of decreasing reactivity towards nitration
Chapter 9 Solutions
Experimental Organic Chemistry: A Miniscale & Microscale Approach (Cengage Learning Laboratory Series for Organic Chemistry)
Ch. 9.2 - Prob. 1ECh. 9.2 - Prob. 2ECh. 9.2 - Prob. 3ECh. 9.2 - Prob. 4ECh. 9.2 - Prob. 5ECh. 9.2 - Prob. 6ECh. 9.2 - Prob. 7ECh. 9.2 - Prob. 8ECh. 9.2 - Prob. 9ECh. 9.2 - Prob. 10E
Ch. 9.2 - Prob. 11ECh. 9.2 - Prob. 12ECh. 9.2 - Prob. 13ECh. 9.2 - Prob. 14ECh. 9.2 - Prob. 15ECh. 9.2 - Prob. 16ECh. 9.2 - Prob. 17ECh. 9.2 - Prob. 18ECh. 9.2 - Prob. 19ECh. 9.2 - Prob. 20ECh. 9.2 - Prob. 21ECh. 9.2 - Prob. 22ECh. 9.2 - Prob. 23ECh. 9.2 - Prob. 24ECh. 9.3 - Prob. 1ECh. 9.3 - Prob. 2ECh. 9.3 - Prob. 3ECh. 9.3 - Prob. 4ECh. 9.3 - Prob. 5ECh. 9.3 - Prob. 6ECh. 9.3 - Prob. 7ECh. 9.3 - Prob. 8ECh. 9.3 - Prob. 9ECh. 9.3 - Prob. 10ECh. 9.3 - Prob. 11ECh. 9.3 - Prob. 12ECh. 9.3 - Prob. 13ECh. 9.3 - Prob. 14E
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- Classify the following sigmatropic rearrangement and determine whether it takes place readily under thermal or photochemical reaction conditions.arrow_forward11.; (a) Similar to alkanes, hydrogen gas can undergo radical bromination according to the reaction below. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46 kcal·mole', for H-Br is 88 kcal'mole and for H-H is 104 kcal'mole'. hv H-H + Br-Br 2 H-Br (b) Calculate the overall AH for the above propagation steps (show all work).arrow_forwardp-Fluoronitrobenzene is more reactive toward hydroxide ion than is p-chloronitrobenzene. What does this tell you about the rate-determining step for nucleophilic aromatic substitution?arrow_forward
- An enolate is a very strong nucleophile. Bromine is a strong electrophile, so it can react withmuch weaker nucleophiles. Give mechanisms for the reactions of bromine with cyclopenteneand with phenol, which are both much weaker nucleophiles than an enolatearrow_forwardThe high reactivity of alkyl halides can be explained in terms of nature of C-X bond which is highly polarized covalent bond due to large difference in the electronegativities of carbon and halogen atom. This polarity is responsible for the nucleophilic substitution reactions of alkyl halides which mostly occur by Swa and Swa mechanisms. Sy reaction is a two-step process and in the first step, R-X ionizes to give carbocation (slow process). In the second step, the nucleophile attacks the carbocation from either side to form the product (fast process). In Swi reaction, there can be racemization and inversion. Swi reaction is favored by heavy (bulky) groups on the carbon atom attached to halogens. i.e., R,C-X>R;CH-X>R-CH,X>CH,X. In Sna reaction, the strong nucleophile OH attacks from the opposite side of the chlorine atom to give an intermediate (transition state) which breaks to yield the product (alcohol) and leaving (X) group. The alcohol has a configuration opposite to that of the…arrow_forwardBromo compound N can undergo substitution with nucleophiles X to give mixtures of products O and P as shown below. Explain how this is possible, and suggest an explanation for the observation that the proportion of product P increases with increasing solvent polarity. F N Br X- O X ...X F Parrow_forward
- Given the following compounds: 1-bromopropane, 1-chloropropane, 2-chlorobutane, and 1-chloro-2-methylpropane Order them based on their reactivity against the SN2 reaction (decreasing). Will the substitution proceed faster with CH3O- or CH3S-? Reason for it.arrow_forwardWhich compound(s) is (are) best suited for nucleophilic aromatic substitution reactions?arrow_forwardc) For the following substituted benzenes, please rank their relative rates of reactivity in an EAS substitution reaction with HNO3/H2SO4, where 1 = fastest, or most reactive, and 6 = slowest, or least reactive. OMe Br Br NO2 `NO2arrow_forward
- 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_forwardRank the attached compounds in order of increasing reactivity in asubstitution reaction with −CN as nucleophile.arrow_forwardPossible alternative brominations include: Veratrole (1,2-dimethoxybenzene) to 1,2-dibromo-4,5-dimethoxybenzene; 4-Methylacetanilide to 2-bromo-4-methylacetanilide; 2-Methylacetanilide (made in experiment S.1) to 4-bromo-2-methylacetanilide; Vanillin to 5-bromovanillin; Acetanilide to 4-bromoacetanilide; a. b. C. d. e. EXPERIMENT S4: BROMINATION OF AROMATIC COMPOUNDS Certain other acetanilides made in experiment S.1 may also be used as precursors in this experiment. Estimated time: 1 afternoon Associated learning goals: Section 6, LG 6.6; Section 7, LG 7.2 and 7.4 Pre-lab report: complete the standard report form, and answer the following questions. In this experiment, molecular bromine (Br2) is generated from the redox reaction of potassium bromate with hydrobromic acid. Write a balanced equation for this process. Briefly outline the mechanism by which Br2 brominates your aromatic compound. Why do the bromine atoms end up at the positions indicated rather than anywhere else in the…arrow_forward
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