Chapter 10, Problem 38PP

Draw structures of compounds A to D. Br2 2 eq. KOH in ethanol Compound A (C,H12) Compound B Compound C (elimination product) NANH2 Compound D

Draw the product formed when each starting material is treated with LDA in THF solution at −78 °C.

This compound is treated with two different oxidizing reagents: either H2CrO4 and H2SO4, or with PCC. Draw the major organic product for each of the oxidation reactions.  1. Draw the product when the compound is oxidized with H2CrO4 and H2SO4. 2. Draw the product when the compound is oxidized with PCC.

3. Draw the products formed when terpinolene, a fragrant molecule found in many cannabis strains, is treated with ozone followed by Zn, H₂O. terpinolene

Compound Y has molecular formula C,H12. Hydrogenation of compound Y produces methylcyclohexane. Treatment of compound Y with HBr in the presence of peroxides produces the following compound: Br Draw the product(s) when compound Y undergoes ozonolysis.

32 Draw a structural formula for the product formed by treatment of butanal with each set of reagents. (a) H₂/transition metal catalyst (b) NaBH, then H₂O + (c) Ag(NH₂), (Tollens' reagent) (d) K₂Cr₂O/H₂SO4 (d

Aziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60° bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y.

What product is formed when each compound is treated with NaH? Each of these acid–base reactions was a step in a synthesis of a commercially available drug.

Answer the following questions about curcumin, a yellow pigment isolated from turmeric, a tropical perennial in the ginger family and a principal ingredient in curry powder.a.In Chapter 11, we learned that most enols, compounds that contain a hydroxy group bonded to a C=C, are unstable and tautomerize to carbonyl groups. Draw the keto form of the enol of curcumin, and explain why the enol is more stable than many other enols. b.Explain why the enol O—H proton is more acidic than an alcohol O—H proton. c. Why is curcumin colored? d.Explain why curcumin is an antioxidant.