b. The compound below is an example of a steroid. Assign the stereochemistry at each asymmetric carbon. Using a 3D model as a guide, briefly speculate as to why a nucleophile would attack the ketone stereoselectively from the back (bottom) face as represented below.
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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 [ ?10. Explain the reaction shown below. Include the following pieces in your explanation. Identify the electrophile and the nucleophile. Draw a curved arrow mechanism for this reaction. (Assume an acidic work-up). Explain the electron flow. Indicate any regiochemical or stereochemical preferences. one b. c. d. LIAIH4 OH oneAcyl 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 HCI / H2O `NH2 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. opy aste Previous Next
- 4. Explain the reaction shown below. Include the following pieces in your explanation. a. Identify the electrophile and the nucleophile. b. Draw a curved arrow mechanism for this reaction. (Assume an acidic work-up). Explain the electron flow. C. d. Indicate any regiochemical or stereochemical preferences. H₂C OCH₂ H+ HO,... CH₂OHAnswer both of the following questions precisely, succinctly, and with correct grammar. A. Explain in detail why sodium methoxide (NaOCH,) is more reactive than methanol (HOCH,) in S,2 reactions. Draw two analogous S,2 reactions, one for each reagent, to illustrate your answer. B. In principle, the conversion of an alkyl bromide into the corresponding alkene can be accomplished either by an El or an E2 pathway. Explain in detail why the E2 mechanism usually is preferred.Draw structures for the carbonyl electrophile and enolate nucleophile that react to give the enone below. TH • You do not have to consider stereochemistry. • Draw the enolate ion in its carbanion form. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple reactants using the + sign from the drop-down menu. C opy ate OF ChemDoodle
- Draw the structure(s) of the major organic product(s) of the following reaction. 1. NaOCH3 / CH3OH H3C CH3 2. 1 eq. 2-bromo-2-methylpropane • You do not have to consider stereochemistry. • Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr)2 derived from N(i-Pr),. • If no reaction occurs, draw the organic starting material. • If substantial starting material is present at the end of the reaction, include it in the products. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. Draw the structure(s) of the major organic product(s) of the following reaction. Aqueous NaHCO3 0° C 1 eq. Cl2 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If the reaction produces a racemic mixture, draw both stereoisomers. • If no reaction occurs, draw the organic starting material. • Draw one structure per sketcher. Add additional…Alkyne Reagents. Provide stereochemically accurate product(s) in the boxes provided or appropriate reagents in the spaces below to make the following scheme work. (You may not be able to do all of this yet based on where we are in the lecture....and it's ok, skip what you don't know OR use the alkyne scheme to try and predict the products in the boxes...your choice.)10. Explain the reaction shown below. Include the following pieces in your explanation. a. Identify the electrophile and the nucleophile. b. Draw a curved arrow mechanism for this reaction. (Assume an acidic work-up). Explain the electron flow. Indicate any regiochemical or stereochemical preferences. C. d. LIAIH4 OH
- [Review Topics] [References) Draw a structural formula for the major product of the acid-base reaction shown. H2N. HCI (1 mole) (1 mole) You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na", I, in your answer. • In those cases in which there are two reactants, draw only the product from the compound that reacts. C P. opy eate4) a) Attempting to alkylate t-Butylchloride with the enolate of acetone gives an undesired product. Draw the structure of the product and explain why it forms. b) [self-study not grade: Compare the difference between the alkylation of ketones and the alkylation with malonic ester or acetoacetic ester. Provide a reason for to explain why aldehydes are rarely used in this kind of alkylation reaction. ]How does increasing base, solvent, or alkyl halide or aptly halide + base affect or decreasing them affect the reaction rate for e2/e1 and sn2/sn1? Please provide examples