NH 2 O O O O OCH (6 pts) Provide an acceptable name for each of the following compounds: NH 2 COOH HOOC COOH. piperidine
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1 CEMISTRY MIDTERM # 4 April 1, 2003 Statistics: Average: 87 pts (72%); ighest: 116 pts (97%); Lowest: 49 pts (41%) umber of students performing at or above average: 13 (62%) 1. (9 pts) Mark as true (T) or false (F) the following statements. Do not explain! (F) Fischer esterification occurs only in strongly basic conditions; (F) Amides are less reactive than acid chlorides but more reactive than esters; (T) Saponification is the process of base-catalyzed hydrolysis of esters; (F) Lactones are intramolecular amides; (F) Primary amines are molecules in which the amino group is bound to a primary carbon; (T) The value of pk b decreases with an increasing strength of the base; (T) Primary amines can serve as hydrogen bond donors and hydrogen bond acceptors; (T) Secondary amines are stronger bases than primary amines; (F) Michael addition reactions give 1,2-addition products; 2. Circle all that apply: A. (3 pts) The following reactions CAT be used to generate esters: a. Base-catalyzed reaction of carboxylic acid and alcohol; b. Reaction of acid chloride and alcohol; c. Reaction of amide and alcohol; d. Baeyer-Villiger oxidation of ketones; B. (3 pts) The following reactions D T occur with an intermediate formation of enolates: a. Fischer esterification; b. Claisen condensation; c. Dieckmann cyclization; d. Michael addition; C. (3 pts) The following compounds D T decarboxylate upon ing: a. β-ketoacids; b. γ-dicarboxylic acids; c. β-dicarboxylic acids; d. γ -hydroxyacids; 3. (6 pts) Provide an acceptable name for each of the following compounds: 2 C 3 cis-3-aminocyclopentanol phthalic anhydride 6-hexanolide methyl acetoacetate -ethyl-methylcyclohexylamine butylmethylmalonic acid 4. ( pts) Provide the structure of each of the following compounds: C C 2 C C C (E)-2,3-dimethylbutenedioic acid 2,2-dibromocyclopropanamine piperidine 4-methyl-2,6-pyridinedicarboxylic acid -(dimethylamino)-3-hexynoic acid
2 . ( pts) Rank the following compounds in order of increasing basicity. Do not explain! A. Cyclopentylamine; B. -methylcyclopentylamine; C. Aniline; D. 4-nitroaniline; E. Sodium amide; D < C < A < B < E 6. ( pts) Rank the following compounds in order of increasing acidity. Do not explain! A. Trichloroacetic acid; B. Trifluoroacetic acid; C. Propanoic acid; D. Isopropanol; E. Isopropylamine; D < C < A < B < E 7. Write a complete equation for each of the processes indicated below (TE: Do not write mechanisms!!). A. (4 pts) Reaction of maleic anhydride (cis-butenedioic acid anhydride) with ethanol. + C 2 C 2 B. (4 pts) Saponification of γ-butyrolactone. K 2 K C. (4 pts) Reaction of n-butyl bromide with sodium cyanide, followed by acid hydrolysis; 1. ac C , D. (4 pts) Reaction of ethyl acetate with ethyl formate in the presence of ac 2 /C 2 ; ac 2 + C 2 C 2 C 2 C 2 8. (18 pts) Predict the principal organic product in each of the following reactions: 1. Mg/ether 2. C C C 1. LiAl C 2 C C C 1. ac 2 /C 2 2. C 1. 2 /P C Cl C 3 2 pyridine C 3 C C 3 C 3 2 S 4 CC 3 C 3 1. C 3 Mg
3 CC 2 CC 2 1. ac 2 / C 2 2. C 2 C CC 2 1. LDA, 3 C C 3 CC 3 9. (16 pts) Fill in the blanks in the following scheme: 1. ac/dms , C 3 2 S 4 I C CC 3 1. ac 3 / C C 3 SCl 2 CCl pyr 1. a , 1. ac 3 / C 3 2. C 3 I C (6 pts) Propose a mechanism for the following reaction: C 2 C 3 + C C 2 C 3 Cl C C 3 + C C 3 C C 3 C 2 C C C 2 C C C 2 C C 3 - C Suggest a plausible synthetic sequence for each of the following transformations. Use any necessary organic or inorganic reagents. A. ( pts)?? C 3
4 1. 2 ac/dmf , 3. 2 C 3, 2 S 4 3 CC?? C 2 C 2 CC 3 ac 3 C 3 C 3 B. ( pts) 1. ac/dmf , 3. C 2, 2 S 4 CC2 ac 2 C 2 C 2 C 2 C Use the acetoacetic or malonic ester synthesis to prepare each of the following compounds. Employ any other necessary organic or inorganic reagents. A. ( pts) 3-ethyl--hexen-2-one; C 2 1. ac 2 /C 2 2. C 2 3. ac 2 /C 2 4. B. (4 pts) Cyclopentanecarboxylic acid; C 2 1. K , - C 2 C 2 C 2 1. ac 2 /C 2 2. C 2 C CC 2 1. K , - C 2 C 13. (6 pts) The 1 MR spectra of two isomeric compounds, A and B, with molecular formula C are shown below. Assign the correct structure for each isomer. Compound A C
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