Consider the following reaction sequence: Part: 0/3 Part 1 of 3 OH pyridine [1] -SO,CI NaOCH,CH, [2] Draw the structure of the tosylate formed in Step [1] of the reaction sequence shown, including appropriate stereochemistry. Do not use abbreviations for any portion of the tosylate structure. Click and drag to start drawing a structure. ☐ :
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- Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. H3C. ... NH2 HCI/H₂O reflux • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one. + 4 n [ ?Draw the structure of the organic product that is formed when the compound shown below is treated with the following reagents: 1) TsCl, pyridine; 2) NaCN. Interactive 3D display mode H₂Cl OH Draw the molecule on the canyas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single beDraw the structure(s) of the major organic product(s) of the following reaction. 1. Dry Et₂O 2. aqueous H₂SO, at º MgBr + H₂C- You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu. still 2 4 2000 [ ] ChemDoodleⓇ < 36
- 2. Complete the following: Stereochemistry and regiochemistry may be important. type a) NaOH (aq) b) neutralize ➤ OMe a) LiAlH4, ether NMe2 f) b) H3O+ type b) a) HS SH ZnCl2, H+ b) Raney Ni g) type formation of thioacetal/desulfurization HO type Hell-Volhard-Zelinsky Reaction h) CO₂Et type Wittig Reaction H H₂N OEt OH DCC, CH2Cl2 Ph type a) NaH, THF CO₂Et d) b) BnBr, THE CO₂Et c) NaOH(aq); HCl(aq); heat type type HO type (COCI)2, cat DMF CH2Cl2 j) CI type a) NHEN b) LiAlH, THE c) H3O+ CO₂Me CO₂Mekeferences Draw the structure(s) of the major organic product(s) of the following reaction. H. PPH3 THE • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If the reaction produces a racemic mixture, draw both stereoisomers. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Include anionic counter-ions, e.g., I-, in your answer, but draw them in their own sketcher. C opy asteCurved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the arrows to draw the intermediate and product in this reaction or mechanistic step(s). Include all lone pairs and charges as appropriate. Ignore stereochemistry. Ignore inorganic byproducts. :OH Draw Product -HCI Draw Tetrahedral Intermediate
- [References] Draw the structure(s) of the major organic product(s) of the following reaction. CH3MGI 1. Dry Et,0 H. 2. aqueous HCI at 0° You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the sign from the drop-down menu. C opy aste - [F ChemDoodle removeAcyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. CH3OH H3C CI • • • • You do not have to consider stereochemistry. Include all valence lone pairs in your answer. Do not include counter-ions, e.g., Na+, I", in your answer. In cases where there is more than one answer, just draw one.2) Complete the following: Stereochemistry and regiochemistry may be important. a) b) C) d) e) type type type OCH 3 type type OH CH₂OH EAS - Nitration H₂ Lindlar Catalyst KMnO4 NaOH/H₂O + OCH3 "OCH 3 Br CHO OH OH f) g) h) i) j) type type OCH3 type type type OH Bronsted-Lowry acid base chemistry CO₂Me OH K Friedel-Crafts Acylation NO₂ a) LIAIH,₁, ether b) H₂O* H₂SO4 OH OH NH₂
- Draw the products of the reaction shown below. Use wedge and dash bonds to indicate stereochemistry. Ignore inorganic byproducts. 1. Os04 2. NaHSO3, H3O Select to Draw Select to DrawDraw the structure(s) of the major organic product(s) of the following reaction. но NACN aqueous H,SO, • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu. C P. opy aste ChemDoodledon 13. (1) Draw the (E)- and (Z)- isomers of 1,3-dichloro-2-methylbut-2-ene. Using curved arrows, draw (a) an SN2 mechanism and (b) and SN1 mechanism for the substitution reaction shown below. Br ) Draw the organic product(s) formed in the following reactions: 1)0, by 2) Zn. H,0 MShow a sequence of reactions that could be used to synthesize the following compound. You must start from 3-pentanol. No mechanisms needed (HINT: You wil need to bring together more than one of the reactions you have seen in Modules 3 and 4]