Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 9.1, Problem 5P
Rank the following alkyl bromides from most reactive to least reactive in an SN2 reaction: 1-bromo-2-methylbutnne, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, and 1-bromopentnne.
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Rank the following alkyl bromides from most reactive to least reactive in an SN2 reaction: 1-bromo-2-methylbutane, 1-bromo-3-methylbutane, 2-bromo-2-methylbutane, and 1-bromopentane.
Draw the four resonance structures formed during bromination of methoxybenzene, CH3OC6H5, with Br2/FeBr3 to give para-bromomethoxybenzene and then circle the most stable resonance form.
Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.
Chapter 9 Solutions
Organic Chemistry
Ch. 9.1 - Prob. 3PCh. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.2 - Prob. 8PCh. 9.2 - Prob. 9PCh. 9.2 - Prob. 10PCh. 9.2 - Prob. 11PCh. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 14PCh. 9.2 - Prob. 16P
Ch. 9.3 - Prob. 17PCh. 9.4 - Prob. 18PCh. 9.5 - Prob. 19PCh. 9.5 - Prob. 20PCh. 9.5 - Prob. 21PCh. 9.5 - Prob. 22PCh. 9.6 - Prob. 23PCh. 9.6 - Prob. 24PCh. 9.6 - Which of the following reactions take place more...Ch. 9.7 - Prob. 26PCh. 9.7 - Prob. 27PCh. 9.7 - Prob. 28PCh. 9.7 - Prob. 30PCh. 9.7 - Under which of the following reaction conditions...Ch. 9.8 - After a proton is removed from the OH group, which...Ch. 9.8 - Prob. 33PCh. 9.9 - Prob. 34PCh. 9 - Prob. 1PCh. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Prob. 37PCh. 9 - Prob. 38PCh. 9 - Prob. 39PCh. 9 - Prob. 40PCh. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 42PCh. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 44PCh. 9 - Prob. 45PCh. 9 - Prob. 46PCh. 9 - Prob. 47PCh. 9 - Prob. 48PCh. 9 - Prob. 49PCh. 9 - Prob. 50PCh. 9 - Prob. 51PCh. 9 - tert-Butyl chloride undergoes solvolysis in both...Ch. 9 - Prob. 53PCh. 9 - Prob. 54PCh. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 56PCh. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 58PCh. 9 - Prob. 59PCh. 9 - Prob. 60PCh. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 62PCh. 9 - Prob. 63PCh. 9 - Prob. 64PCh. 9 - Prob. 65PCh. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 67PCh. 9 - The reaction of chloromethane with hydroxide ion...
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- can you please arrange 1 to 6 alkyl halids from most reactive to least reactive for SN1 and SN2 reaction which alkyl halides will be most reactive and least reactive in the SN2 and SN2 reaction reaction? 1-chlorobutane, 2-chlorobutane, Allyl chloride, 2-chloro-2-methylpropane, 1-chloro-2-methylpropane, 2-bromobutanearrow_forwardarrange the following alkyl bromides in order of decreasing reactivity in an SN1 reaction: 2-bromopropane, 1-bromopropane, 2-bromo-2-methylpropane, bromomethane.arrow_forwardbromobenzene Leaving Groups: Which will undergo a faster SN2 reaction: 2-bromobutane or 2-chlorobutane? Which will undergo a faster SN1 reaction: 2-bromobutane vs. 2-chlorobutane? Provide an explanation for the above predictions. Solvent: droparrow_forward
- Alkyl halides 1-chlorobutane 2-chlorobutane Allyl chloride 2-chloro-2-methylpropane 1-chloro-2-methylpropane 2-bromobutane SN1 conditions = Silver Nitrate in Ethanol 1. Rank the alkyl halides according to their SN1 reactivity. If compounds are similar in reactivity, you may group them in your ranking. Considering substitution, leaving group, temperature, solvent, etc... provide an explanation for each pairwise ranking.arrow_forwardOrder the compounds in each set according to their sn2-displacement reactivity:2-bromo2-methyl butane; 1-bromopentane; 2-bromopentane.arrow_forwardArrange in increasing reactivity in an SN1 reactionarrow_forward
- Q4. Discuss the reagents, conditions, and mechanism of the following reactions. a) Kolbe Reaction b) Williamson synthesis c) Reimer Tiemann reactionarrow_forwardRank the compounds from most reactive to least reactive under conditions of both SN1 and SN2. 1-chlorobutane 2-chlorobutane Ally chloride 2-chloro-2-methylpropane 1-chloro-2-methylpropane 2-bromobutanearrow_forwardWhy do cis-1-bromo-2-ethylcyclohexane and trans-1-bromo-2-ethylcyclohexane form different major products when they undergo an E2 reaction?arrow_forward
- 5. For the following compound rank the proton groups from most reactive to the least reactive in free radical bromination. CH₂ H₂C H₂C CH₂ CH CH3arrow_forwardHh.70.arrow_forward3-Bromocyclohexene is a secondary halide, and benzyl bromide is a primary halide. Both halides undergo SN1 substitution about as fast as most tertiary halides. Use resonance structures to explain this enhanced reactivity.arrow_forward
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