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.
8) Predict the two products that form in following Diels-Alder reaction. Circle the major product.
CH₂O
H
O₂N
CH₂OCH3
H
For SN2
Explain the order in which 1o (primary) alkyl halides reacted and explain why.
The 1o primary alkyl halides are: (see picture below)
1-chlorobutane
1-bromobutane
1-chloro-2butene
benzylchloride
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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- Rank the following compounds from most to least reactive in an SN2 reactionarrow_forwardcan 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_forwardFor SN1 Explain the order in which 1o (primary) alkyl halides reacted (fastest to slowest) and explain why. The 1o primary alkyl halides are: (see picture below) 1-chlorobutane 1-bromobutane 1-chloro-2butene benzylchloridearrow_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_forwardRank the following alkyl halides in term of reactivity in a E2 reaction with NaOH (fastest (1) to slowest (4)): 1-bromo-2,2-dimethylpentane, 1-chloro-2,2-dimethylpentane, 2-chloro-2-methylpentane, and 2-bromo-2-methylpentane.arrow_forwardOrder the compounds in each set according to their sn2-displacement reactivity:1-bromo-3-methylbutane; 2-bromo-2-methylbutane; 3-bromo-2-methylbutane.arrow_forward
- 2-bromo-2-methylbutane with sodium methoxide under SN2/E2 conditions substitution product elimination product both substitution and elimination products no productsarrow_forwardList the following alkyl halides in order of decreasing reactivity toward SN2 reactions (from 1: most reactive to 4: least reactive).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
- Rank group of compounds from most reactive to least reactive toward electrophilic aromatic substitution: :- p-methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p-chloromethylbenzenearrow_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_forwardDraw all the possible constitutional isomers for the molecular formula C4H8Br. Rank them according to their reactivity (i.e. rate) in SN2 reactions.arrow_forward
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