Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
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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Rank the compounds according to their increasing reactivity toward electrophilic substitution.
1. Benzaldehyde
2. o-dimethylbenzene
3. nitrobenzene
4. phenol
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 ✓phenol
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 (3rd 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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- a. Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing both SN2 and SN1 reactions. b. Can it undergo E2 and E1 reactions?arrow_forwardWhich solvents favor SN1 reactions and which favor SN2 reactions?arrow_forwardThrough what mechanism does this reaction primarily proceed? a. SN2 b. E1 c. E2 d. SN1arrow_forward
- Which 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_forwardHow does solvent affect rate of reaction if its increase or decrease in sn1 or sn2arrow_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_forward
- Rank the alkyl halides in order of increasing E2 reactivity. Then do the same for E1 reactivity. CI Br A Carrow_forward2. 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_forward
- Draw the structure for the transition state in each reaction. а. OH2 H20 b. HO, -OH H20arrow_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_forwardUse Zaitsev's Rule to predict the major product of the following E1 reaction? In töm Na Br XXXX Select one: a. I b. Il C. ||| d. IV IVarrow_forward
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