The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
10th Edition
ISBN: 9781118875780
Author: James W. Zubrick
Publisher: WILEY
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Chapter 3, Problem 2E
Interpretation Introduction
Interpretation: Look up the Freidel-Crafts acylation reaction of toluene with acetyl chloride and the product(s) formed in a handbook. The product is not named as a substituted toluene, even though the acetyl group did substitute for a hydrogen on the toluene ring is to be explained.
Concept Introduction:
Friedel Crafts reaction is a
FriedelCrafts reactions are of two main types: alkylation reactions and acylation reactions and both proceed by electrophilic aromatic substitution.
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Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.
5. Optically pure 2-octyl sulfonate was treated with varying mixtures of water and dioxane, and the
optical purity of the resulting product (2-octanol) was found to vary with the ratio of water to
dioxane, as shown in the following table (J. Am. Chem. Soc. 1965, 87, 287-291). Given that
dioxane possesses fairly nucleophilic oxygen atoms, provide a complete mechanism that
explains the variation in in the product's optical purity due to changes in solvent composition.
Hint, the solvent is doing more here than just dissolving.. it is partaking in the reaction.
Solvent Ratio (water : dioxane)
25:75
50: 50
75: 25
100 :0
Optical purity of (S)-2-octanol
77%
88%
95%
100%
H20
он
(R)-2-Octyl sulfonate
(optically pure)
(S)-2-Octanol
(dioxane)
VII. 1-bromo-3-methyl-2-butene undergoes nucleophilic substitution reaction in
both ethanol and sodium ethoxide/DMSO mixture.
(1) Please write all organic substitution products for each of the two reactions, if two
products are formed in a reaction, assign the major product, assuming that the
reaction is under kinetic control
(2) What is the most likely mechanism for each reaction? (giving the name of
mechanism is sufficient).
Chapter 3 Solutions
The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
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- Suggest an explanation for the fact that the order of reactivity of the halides toward n-butylbrosylate in acetone is Cl” > Br” > I~ when (C4H9)4N* is the cation of the halide salt butI” > Br” > Cl” when Li’ is the cationarrow_forwardIn this study, the researcher compared S N 2 and E2reaction rates for four substrates. Three of the substrates had a second halogen on the bposition in the molecule. This work also compared the behavior of two nucleophiles:dianion I and II. You should read the abstract and look at Scheme 1 (p. 3082) and Table 4(p. 3086). Abstract: The gas-phase reactions of benzoate and phenolate containing dianions with a series of ‚-substitutedalkyl bromides (X-CH2CH2Br, X ) H, F, Cl, Br) have been studied in a quadrupole ion trap mass spectrometer.Branching ratios between SN 2 and E2 products were measured and rate constants were determined. The‚-halogens increase both the S N 2 and E2 rates, but the effect is greater for the latter process and thereforethese substituents lead to an increase in the amount of elimination. The kinetic data for the SN 2 reactions canbe analyzed via a two-parameter, linear free-energy relationship and the results indicate that field-effects (i.e.,electron-withdrawing…arrow_forwardIn this study, the researcher compared S N 2 and E2reaction rates for four substrates. Three of the substrates had a second halogen on the bposition in the molecule. This work also compared the behavior of two nucleophiles:dianion I and II. You should read the abstract and look at Scheme 1 (p. 3082) and Table 4(p. 3086). Abstract: The gas-phase reactions of benzoate and phenolate containing dianions with a series of ‚-substitutedalkyl bromides (X-CH2CH2Br, X ) H, F, Cl, Br) have been studied in a quadrupole ion trap mass spectrometer.Branching ratios between SN 2 and E2 products were measured and rate constants were determined. The‚-halogens increase both the S N 2 and E2 rates, but the effect is greater for the latter process and thereforethese substituents lead to an increase in the amount of elimination. The kinetic data for the SN 2 reactions canbe analyzed via a two-parameter, linear free-energy relationship and the results indicate that field-effects (i.e.,electron-withdrawing…arrow_forward
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