Question

1. Write the structural formula of each of the following co (1) m-chlorobenzoyl chloride; (b) p-ethylbenzamide: (©) (e) 2-ethyl-1-butanamine; (f) dibenzylamine; (g) a B-lacta the following compounds: (28 pts) Pethylben (s) acetoacetic ester; (d) diethyl malonate: of each of the following reactions: (30 pts) 2. Identify the principal organic product of each of the (a) acetic anhydride and 2-pentanol (b) 4-methyl-3-penten-2-one and ammonia in water solut er solution (c) acetophenone (methyl phenyi ketone) and benzalder (d) methyl butanoate and LDA (lithium diisopropylamide) in (e) butylamine and excess 1-iodobutane (f) acetanilide and LiAlHe in diethyl ether, followed by addition of water. ketone) and benzaldehyde + KOH in ethanol solvent diisopropylamide) in THF solution, then ethyl iodide the following, starting from the compound indicated and 3. Show efficient syntheses for each of the following, starting from th using any other needed reagents. (49 pts) (a) acetyl chloride, from ethanol (b) propyl propanoate, from 1-propanol (c) 2-heptanone, from 1-bromobutane (d) caproic acid (hexanoic acid) by the malonic ester synthesis (e) p-aminobenzoic acid (PABA), from p-methylaniline (1) p-FC6H4CCH2CH3, from benzene (g) 1,3,5-tribromobenzene, from benzene 4. Prontosil is a sulfa drug effective against staphylococcus bacteria. It can be prepared from sulfonilamide and m-diaminobenzene. Show how. (10 pts) HN-

Answer 1

«) m-chloro fenaypyl chlrid Cl b-eenemide (c) acefaehe 4sfez_ die-Meloncle. ce 2- el--bitemarie dilonylame .cH3

DA e CH-CH-C-C- +CH3-Clb- 14 CH2- -G3 CH3CH2)2-C 13CHC .Cl-C)2-Ctj CH3 -CH 2-CH - N LitH