Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 8.2, Problem 8P
Which reaction in each of the following pairs occurs faster?
- a. CH3CH2Br+H2O or CH3CH2Br+HO
- b. CH3CH2CI+CH3O- or CH3CH2CI+CH3OH
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Rank the species in each group in order of increasing nucleophilicity.a. CH3CH2S-, CH3CH2O-, CH3CO2- in CH3OHb. CH3NH2, CH3SH, CH3OH in acetonec. -OH, F-, Cl- in acetoned. HS-, F-, Cl- in CH3OH
Identify the stronger nucleophile in each pair.
a. NH3,−NH2
b. CH3NH2, CH3OH
c. CH3CO2−, CH3CH2O−
Which SN1 reaction is each pair is faster?
А.
CH,OH
CH;OH
B.
Br CH CHOН
eBr
OMSO
Br CH,CH OH
CH,CH,OH
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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- Draw the product of each reaction. wCH3 HBr CH3CH,OH c. CH;CH2 ČHĄCH, a. H2SO4 CH [1]-CN [1] CH30 b. d. CH,CH2 CH,CH2 [2] H20 [2] CH3OHarrow_forwardDecide on the mechanism for each substitution, and then pick the solvent that affords the faster reaction. a.(CH3CH2)2CClCH3 + CH3OH in CH3OH or DMSO b.CH3CH2CH2Br + −OH in H2O or c. DMF (CH3CH2)2CHCl + CH3O− in CH3OH or HMPAarrow_forwardWhich is the better leaving group in each pair?a. Cl-, I-b. NH3, -NH2c. H2O, H2Sarrow_forward
- c. Which reacts faster in an Sy1 reaction? CH3 CH3 CH;CHCHCH3 or CH;CH,CCH3 1. Br Br d. Which reacts faster in an E2 reaction? Br Br orarrow_forwardFor Nos. 63-70 Choose: A -if the indicated property/behavior in item I is greater than in item II B-if the indicated property/behavior in item I is less than in item II. C- if the indicated property/behavior is equal in item I and item II. D- if the indicated data is insufficient to make a comparison. 63. Reactivity toward Nucleophilic Addition Reaction I. FCH₂CHO II. CH3CHOarrow_forwardA -if the indicated property/behavior in item I is greater than in item II B-if the indicated property/behavior in item I is less than in item II. C- if the indicated property/behavior is equal in item I and item II. D- if the indicated data is insufficient to make a comparison.arrow_forward
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- 6. Draw the major neutral product of each reaction and indicate whether the predominant mechanism is S1 or S2 in each case. A. B. C. D. E. Br Br CI HO NaSMe DMF NaN3 DMF IOH OH KCN THFarrow_forwardRank the species in each group in order of increasing nucleophilicity. a. CH3CH2S−CH3CH2O−, CH3CO2− in CH3OH b. CH3NH2, CH3SH, CHOH in acetone c.−OH, F−, Cl− in acetone d. HS−, F−, Cl− in CH3OHarrow_forwardWhat is the product of the illustrated mechanism? A A B B C C D D HAC H₂C A H- ,CH 3 O: H3C. CH3 ? H3C H3C. , CH 3 H3C. H3COH ధర్మం , వ O: HAC H3C P CH3 H B D CH3arrow_forward
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