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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- 20.71 Propose an efficient synthesis for each of the following transformations: - (a) (b) MeO OMe Br Br (c)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)19.69 Propose an efficient synthesis for each of the following transformations: (a) (b) (c) Br Br -C MeO OMe
- 19.73 Propose an efficient synthesis for each of the following transformations: (d) OH -CN 0-0 Q-8" (e)Aspartame, the sweetener used in the commercial products NutraSweet and Equal, is 200 times sweeter than sucrose. What products will be obtained ifaspartame is hydrolyzed completely in an aqueous solution of HCl?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 H2O
- 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,COOH22) 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