CH, - CH,OH CHCL, 27 76 75 74 i3 72 ppm TMS & ppm (a) 'H NMR spectrum (300 MHz). (b) "C NMR data: ô 21.3, 65.4, 127.1, 1273, 127.7, 129.7, 137.3, 138.1, 139.8, 140.8.

Choose the best sequence of reactions for the transformation given. Semicolons indicate separation steps to be used in the order shown. A) H,O*; SOCl,; SOCI₂; C6H5CO2CH3 || CoH5CH2CNHCH3 CHÍNH, B) HO/H,O; PBrạ; Mg; CO,; H,O*; SOC1,; CH,NH, C) LiAlH; H₂O; HBr; Mg; CO₂; H₂O+; SOCI₂; CH₂NH₂ D) None of these would yield the desired product

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)

Give a detailed mechanism including all resonance isomers for intermediates (show electron flow) for the Friedel-Crafts reaction Expt. 29.4-micro: Friedel-Crafts Synthesis of 1,4-t-Butyl-2,5-dimethoxybenzene.  NOTE:  It is likely the mechanism from reactants to only 1-t-butyl-2,5-dimethoxybenzene.  I want a complete mechanism showing all steps and resonance isomers for the synthesis of the dialkylated product.

(c) (d) 15.7 Complete these reactions involving lithium diorganocopper (Gilman) reagents. (b) Br CuLi 2 CuLi Hou Culi نس) . Culi 2 ether ether ether ether 0

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).

01:50 4G File Details 4CH003/UM1: Fundamentals of... Introduction NaBH4 OH C=0 H benzophenone diphenylmethanol Ketones are readily reduced to secondary alcohols by reaction with sodium borohydride. The aim of this experiment is to determine the time required to effect the complete conversion of the ketone, benzophenone to diphenylmethanol at room temperature. This investigation may be achieved by isolating and analyzing the reaction product after different reduction times. Infrared spectroscopy affords a convenient method of analysis; by comparing the IR spectrum of the crude reaction product at different time intervals one would expect to see the intensity of the hydroxyl absorption peak increase relative to that of the original carbonyl peak. From this you can deduce the optimum time for the reduction process at room temperature. Procedure Note the "reduction time" that the demonstrator assigns to your group. Different groups will be assigned different times, eithert = 2.5 minutes,…

Suggest reasonable mechanisms for the following reactions:

Q4. Stabilized enolates and their surrogates. (a) Complete the following FOUR reaction schemes by drawing structures for the relevant stabilized enol, enolate or surrogate intermediates (A to D), and for the eventual organic products (E to H). (i) (ii) (iii) (iv) EtO CHO Me,SICI, Et N NaOEt EtOH HCO₂Et, NaOEt EtOH (i) t-BuNH, molecular sieves (ii) LDA A B C D MeBr, TICI 1. NaH 2. Mel 1. NaH 2. RBr 1. Me,SICI 2. RCHO, CsF E F G H

The 1H-NMR spectrum shown is that of a compound with formula CHCIO. This compound has an IR absorption at 1724 cm 1. Propose a structure. 6 4 ppm 0 Spectra images are reproduced by permission from Sigma-Aldrich and the National Institute of Advanced Industrial Science and Technology (SDBSWeb: http://riodb01.ibase.aist.go.jp/sdbs/, 8/26/05, 2/7/09, 2/13/09, 3/10/09). (Note: Aldehyde protons (CHO) often show very small coupling constants to adjacent hydrogens, so the splitting of aldehyde signals is not always apparent.) . You do not have to consider stereochemistry. • In cases where there is more than one answer, just draw one.