Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 8, Problem 52P
- a. Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing either SN2 or SN1 reactions.
- b. b. Can it undergo E2 and E1 reactions?
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a. Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing both SN2 and SN1 reactions. b. Can it undergo E2 and E1 reactions?
Consider 3-iodo-2,3-dimethylpentane and 3-iodo-2methylpentane.
a. which reacts faster in an Sn2 reaction? Explain.
b. which reacts faster in an E2 reaction? Explain.
Substitution and Elimination (Please draw the structures involved in the reactions)
A. Which will react more rapidly via SN1? 1-bromo-2,2-dimethylpropane or 2-bromo-2-
methylbutane? Explain.
B. Which will react faster via SN2? 1-chlorocyclohexane or 1-chloro-1-methylcyclohexane?
Explain.
Chapter 8 Solutions
Essential Organic Chemistry, Global Edition
Ch. 8.1 - Prob. 2PCh. 8.1 - Does increasing the energy barrier for an SN2...Ch. 8.1 - Arrange the following alkyl bromides in order from...Ch. 8.2 - Prob. 7PCh. 8.2 - Which reaction in each of the following pairs...Ch. 8.2 - Prob. 9PCh. 8.2 - Prob. 11PCh. 8.3 - Draw the substitution products that will be formed...Ch. 8.4 - Arrange the following alkyl halides in order from...Ch. 8.5 - Prob. 14P
Ch. 8.5 - Which of the following reactions will go faster if...Ch. 8.6 - After a proton is removed from the OH group, which...Ch. 8.6 - Draw the product of each of the following...Ch. 8.9 - Prob. 20PCh. 8.9 - Prob. 21PCh. 8.11 - Why do the SN1/E1 reactions of tertiary alkyl...Ch. 8.11 - Prob. 23PCh. 8.11 - Prob. 24PCh. 8.12 - Prob. 25PCh. 8.12 - Prob. 26PCh. 8.12 - Prob. 27PCh. 8.12 - a In which solvent would tert-butyl bromide...Ch. 8.13 - What would be the best way to prepare the...Ch. 8 - Methoxychlor is an insecticide that was intended...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Explain how the following changes would affect the...Ch. 8 - Prob. 38PCh. 8 - Draw the major product obtained when each of the...Ch. 8 - Which alkyl halide in Problem 39 can undergo an El...Ch. 8 - Prob. 42PCh. 8 - Prob. 43PCh. 8 - Prob. 44PCh. 8 - Prob. 45PCh. 8 - Starting with bromocyclohexane, how could the...Ch. 8 - Prob. 48PCh. 8 - Fill in the blanks in the following chemical...Ch. 8 - For each of the following alkyl halides, indicate...Ch. 8 - Prob. 51PCh. 8 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 8 - An ether can be prepared by an SN2 reaction of an...Ch. 8 - Give two sets of reactants (each set including an...Ch. 8 - Show how the following compounds could be...Ch. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Draw the structures of the products obtained from...Ch. 8 - cis-4-Bromocyclohexanol and...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - In which solventethanol or diethyl etherwould the...Ch. 8 - The pKa of acetic acid in water is 4.76. What...
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- Rank the compounds in each group according to their reactivity toward electrophilic substitution. 1 = most reactive; 3 = least reactive. a. toluene methoxybenzene fluorobenzene b. p-bromonitrobenzene ✓nitrobenzene ✓phenolarrow_forwardWhich set of reagents is used for the Markovnikov addition of water to an alkene without rearrangement? A. BH3, THF followed by H₂O2, NaOH B. H₂O, H₂SO4 C. Hg(O₂CCH3)2, H₂O followed by NaBH4, NaOH D. none of thesearrow_forwardThrough what mechanism does this reaction primarily proceed? a. SN2 b. E1 c. E2 d. SN1arrow_forward
- Which solvents favor SN1 reactions and which favor SN2 reactions?arrow_forwardWhich halide is least reactive towards SN2 reactions ? O a. tert-butyl bromide O b. sec-butyl bromide O c. isopropyl bromide O d. methyl bromide O e. cyclohexyl bromidearrow_forwardHow does solvent affect rate of reaction if its increase or decrease in sn1 or sn2arrow_forward
- 2. Which of the following compounds would react faster in an a. E1 reaction? b. E2 reaction? С. SN1 reaction? d. SN2 reaction? A Barrow_forwardRank the compounds in each group according to their reactivity toward electrophilic substitution. 1 most reactive; 3 = least reactive. a. toluene methoxybenzene fluorobenzene b. benzonitrile ✓p-methylbenzonitrile ✓p-methoxybenzonitrilearrow_forwardDraw the structure for the transition state in each reaction. а. OH2 H20 b. HO, -OH H20arrow_forward
- Rank the alkyl halides in order of increasing E2 reactivity. Then do the same for E1 reactivity. CI Br A Carrow_forwardWhich reaction can be used to carry out the following transformation? A. B. 1. AICI 3 AIC13 2. HCI, Zn(Hg) C. Either is okay D. Neither will workarrow_forwardWhich solvents favor Sy1 reactions and which favor SN2 reactions? a. CH,CH,OH b. CH,CN c. CH,COOH d. CH,CH2OCH½CH3arrow_forward
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