22.35 Propose an efficient synthesis for each of the following compounds using the malonic ester synthesis: R-x (a) (d) OH OH OH Гафон (b) (c) COEF OH +2Br COEF (e)
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- 19.54 Predict the major product(s) from the treatment of acetone with the following: (d) [H], (CH3)2NH, (-H2O) (e) [H], NH2NH2, (-H2O) (f) [H], NH2OH, (-H2O) (g) NaBH4, MeOH (h) RCO3H (i) HCN, KCN (j) EtMgBr followed by H₂O (k) (C6H5)3P=CHCH2CH3 (1) LIAIH, followed by H2O19.69 Propose an efficient synthesis for each of the following transformations: (a) (b) (c) Br Br -C MeO OMe19.73 Propose an efficient synthesis for each of the following transformations: (d) OH -CN 0-0 Q-8" (e)
- 19.40 Propose an efficient synthesis for each of the following transformations: ۵-۵ ۵-۵۰ (a) (c) (e) (9) EtO. OEt می شود (b) لمه mo-od ه - هل (d) OH OH (f)19.73 Propose an efficient synthesis for each of the following transformations: (f) Br H22.1 Which of the compounds shown below has the fewest a- hydrogens? (a) H 여 (b) (c) (d)
- Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.(S)-Glutamic acid is one of the 20 amino acid building blocks of polypeptides and proteins (Chapter 27). Propose a mechanism for the following conversion.15.41 Draw the structures of the aldehydes that might be oxi- dized to yield the following carboxylic acids: (a) COOH (b) CH2COOH ČH3 OH (c) CH,CH=CHCH,COOH
- 22) NM₂2 in N,N-dimethylaniline ( is ortho-para director but it gives meta product in reaction with one of the following reagents. Identify the reagent. a) Br₂ b) c) HNO3 H₂SO4 O ات(a) (b) (c) (d) (e) + Lysine H₂O + Hopi HO3P- HO OH i O: N OH A + HSCH 3 OH acetal formation imine formation enamine hydrolysis acyl substitution 1,4 addition22.5 Propose a synthesis of the compound shown below using the acetoacetic ester synthesis. lloEL ha OEt similar to malonic ester-identify a-carbon, then the alkylation(s)