Draw the major product formed for each reaction. 100 (a) The conjugate acid of triethylamine has a pKa -11, the pKa of the most acidic sites of the substrate is ~20. (b) (c) (d) H3C N CH3 CH3 U-3.H H3C. then CH3l H3C Cu-Li H3C CH3 then H3C OCH3 que travoval nobmotancy cat to) LDA CH3 H3C O then CH3 H3C H CH3 H3C CH3 KOtBu 0 နန်းဝ Si S=0 | 11

Fluvastatin, a cholesterol-lowering drug, can be prepared by thefollowing three-step reaction sequence. Identify intermediates A and Band the final product, fluvastatin.

11. Which compound is the strongest base? (A) m-nitroaniline (B) aniline (C) 4-methylaniline (D) 3-bromo-5-nitroaniline (E) 2,4-dimethylaniline 13 Which of the following compounds has the 12. Which compound is the strongest acid? (A) benzoic acid (B) 4-amino-2-methylbenzoic acid (C) p-nitrobenzoic acid (D) 2,4-dinitroabenzamide (E) 3,5-dinitrobenzoic acid 14 How many H atoms are in the compound:

Please all solution

4. Complete the following assigned textbook problem (with slight variation). Write the letter corresponding to your answer in the box. [2 pts each] Choices may be the correct answer to more than one question or to no question. 19.54 Draw the product formed when phenylacetonitrile (C6H5CH2CN) is treated with each reagent. A CO₂H E B LL F NH₂ G C D NH2 a. [1] DIBAL-H; [2] H₂O b. [1] LiAlH; [2] H₂O c. [1] CH3CH2MgBr; [2] H₂O or H H d. H₂O+ NH2 e. [1] CH,CH,Li; [2] H,O

PQ-22. Which structure is a reasonable intermediate in the acid-catalyzed hydrolysis of ethyl acetate, shown, in dilute aqueous acid? O O (A) H3C-C-OCH₂CH3 OH OH₂ (C) H3C-C-OCH₂CH3 H OH (B) H3C-C-OCH₂CH3 OH2 O (D) H3C-C

2. a) Draw the following: (a) nonanamide (b) N-methyloctanamide (c) (d) N-ethyl-N-propylpropanamide N-ethyl-2,4,6-trimethyldecanamide

Most carboxylic acids have pKa's around 4-5. Keeping in mind what makes and carboxylic acid acidic, which of the following compounds would also have a pKa of ~5? (A) OH (B) OH OH (C) (D) OH

Draw the organic products formed in each reaction (a)-(c)

Etoposide, sold as a phosphate derivative with the trade name of Etopophos, is used for the treatment of lung cancer, testicular cancer, and lymphomas. (a) Locate the acetals in etoposide. (b) What products are formed when all of the acetals are hydrolyzed with aqueous acid?