20 Part 3: Retrosynthesis The cocaine article shows a retrosynthesis in which they you use a dark solid line across a bond and then put the name of the reaction they would use to form that bond. I want you to follow that example and show me the possible retrosynthetic analysis for the following compounds. Please use dark lines and labels across this structure in each place you know how to form that bond. HO HO OH HOH.C CH₂OH

3 The 1H- and 13C-NMR data of an ester of molecular formula C6H10O2 are given below. Also shown are the COSY and HETCOR NMR spectra of the ester. Identify the ester, explaining how you reach your conclusion. 1H-NMR: 7.20-6.90 (1H), 5.85 (1H), 4.16 (2H), 1.88 (3H), 1.31 (3H) ppm 13C-NMR: 166.7, 144.5, 123.0 , 60.2, 18.0, 14.3 ppm

MECHANISM ACTIVITY Base-Induced Ester Hydrolysis (Saponification) NOC XT Step 1: Nucleophilic addition of hydroxide ion to the ester carbonyl group Ahrs MPR R16 H3C. R Part A (1 of 2) Draw the curved arrows for Step 1 of this mechanism. Arrow-pushing Instructions CH3 H-O: ÖH OR' :Ö H-O: O: H H H H 1x xxx CH3 CH3 Step 1 H3C. CH3 за

O NaBH4 Synthesis #2: Select a different set of two substrates and one reagent that could be combined to prepare benzphetamine. tymen Ph Ph Ph Ph NH Ph H O NaBH3CN, H+ 20= ano [H*], NaBH-CN Nucleophile

Assign the proton and carbon NMR spectroscopy for the product of your reaction. Show the proton and carbon NMR peaks. This can be the NMR graph OR a list of peaks labeled 1,2,3 or a,b,c. Label the 1H-NMR spectral data (1,2,3 or a,b,c) and match the peaks to ALL the product molecule's H by labeling them (1,2,3 or a,b,c). Show that you know which 1H-NMR peaks correspond to each hydrogen atoms on your molecule. Label the 13C-NMR spectral data (1,2,3 or a,b,c) and match the peaks to ALL the product molecule's C by labeling them (1,2,3 or a,b,c). Show that you know which 13C-NMR peaks correspond to each hydrogen atoms on your molecule. CO,H NH2*HCI

Calculate the AH for the reaction of the compound below with HBr . Show all your work. Is the reaction endothermic or exothermic? H H- H H H Write the mechanism for the reaction in #3 showing the movement of electrons and any intermediate structures. For the reaction in #4 explain exactly how and why the reaction works as written. Use the appropriate terms and make sure you explain each step completely.

Using curved arrows to show movement of electron pairs, show the mechanism for this reaction.  It is only necessary to draw one resonance structure for any intermediates that are resonance hybrids.  Note that the H atom of the hydroxyl group is acidic enough to be removed by OH–; the first step in the mechanism is a proton transfer.  The general mechanism for base-mediated saponification of an ester is outlined in one of the discussion videos that has been posted for this experiment.

Help ASAP Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Do this by writing all the possible resonance forms for methoxybenzene, including the hybrid. Based on your 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.

All of the following acid-base reactions are reactions that we will study in greater detail in the chapters to follow. Propose the mechanism and then clearly label the acid, base, conjugate acid, and conjugate base: Add curved arrows to show the mechanism for the given reaction. 8.--8-- + OH= 13+ DO нан + H₂O, IU Z 0 a 60 H

What would be the major product of this reaction? Discuss the 1H-NMR spectrum of the product and significant changes between the starting material and your product.