Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 9.4, Problem 18P
Interpretation Introduction
Interpretation:
The
Concept Introduction:
- Unimolecular nucleophilic substitution reaction in which the reversible ionization of alkyl halide in the presence of aqueous acetone or an aqueous ethyl alcohol provides a carbocation as an intermediate, attacked by the nucleophile to form the product is called
- Relative stability of alkyl halide in SN1 reaction:
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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.
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
8) Predict the two products that form in following Diels-Alder reaction. Circle the major product.
CH₂O
H
O₂N
CH₂OCH3
H
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_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_forward8) Predict the two products that form in following Diels-Alder reaction Circle the major product. CH₂O CH₂OCH, H O₂Narrow_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_forwardCH3 OCH2CH2CH CH3 (10) (11) alkyl bromide/ phenyl bromide sodium alkoxide/ sodium phenoxidearrow_forwardCyclopentadienone is a highly reactive ketone. Draw an anti- aromatic resonance structure that explains the reactivity. Include all lone pairs in your structure. + :O:arrow_forward
- bromobenzene 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_forwardbutan-1-ol butanal, CH3 CH2 CH2CHỎ. I eq. NaOCI TEMPO РСС NaOCI НОАС EtMgBr H;O+ H,CrO4 ether or PCC NaOCI НОАС H2CRO4 or PCC excess NaOCI ТЕМPO H,CrO4arrow_forwardRank 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_forward
- Which of the following alkyl halides undergoes the fastest SN2 reaction? 1-iodohexane 1-fluorohexane 1-bromohexane 1-chlorohexane Moving to another question will save this response.arrow_forwardRank the following compounds from most to least reactive in an SN2 reactionarrow_forwardExplain why heats of hydrogenation cannot be used to determine the relative stability of 2-methylpent-2-ene and 3-methylpent-1-ene. A, B, and C, each subjected to hydrogenation. The number of rings and π bonds refers to the reactant (A, B, or C) prior to hydrogenation.arrow_forward
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