Exam 3 - Spring 2007

1 1. (6 Points, 2 points each box) Give the correct name for the following compounds. a) b) c) (CH 3 )N CHO H CH 2 O N OH 2. (8 Points, 2 points each box) Draw the correct structures of the following compounds. a) N-methylpieridne b) D-Glyceraldehyde c) L-Serine d) a-Furanose form of Dglct 2 3. (10 Points) For the following mixed Claisen reaction: a. (3 Points) Give the final product. b. (7 Points) Provide a stepwise mechanism for the formation of the product. Ph O H + CH 3 O 2 CH 23 1) CH 32 ONa 2) , 3 1. 4. (5 Points) Which of the following compounds is the weakest base? H 2 N H 2 N H 2 N H 2 N H 3 CO Cl O 2 N A B C D 5. (6 Points) Propose the structure for the Compound W (a tertiary amine) that has the following 1 HNMR spectrum. Molecular formula of Compound W: C 9 H 13 N IR: 1735 Cm -1 1 HNMR d 7.1, doublet, 2 H d 6.8, doublet, 2 H d 2.8, singlet, 6 H d 2.3, singlet, 3 H Compound W 4 6. (10 Points, 2 points each box) Fil in the boxes with the appropriate mising reagents. CHO O ONH 2 Hofman Elimination 7. (6 Points) Outline an eficient synthesis for the following dipeptide starting with the appropriate amino acids and any other necesary reagents. O N H CH 3 CO 2 H NH 2 5 8. (4 Points, 1 points each) Label each of the following sugars as Reducing (R) or Non?reducing (NR) sugar. O OCH 3 H H OH OH H H H HO O O H H OH OH H H H HO A B O CH 3 OH H HO H O O OH CH 2 O H OH OH H H H HO C CH 2 O HOH OH CH 2 O O D H 9. (6 Points) Outline an eficient synthesis for the following Robinson annulation synthesis starting with the given starting material and any suitable reagents. O O O O 6 10. (15 Points, 5 points each) Outline an eficient synthesis for thre of the following compounds starting with the given starting material and any necesary reagents. ? b) ? O a) O H O CN O OEt O O 7 ? d) ? c) EtO O OEt O NH 2 NH 2 8 11. (24 Points, 2 points each box) Complete the following chemical reactions by filing the boxes with reagents, reactants, or products. For products, only give the major organic ones. CH 32 OH a) b) CH 32 NH 2 O Cl 1) 2) c) d) CH 3 LiAl 4 3) H O OH O H OH CH 2 O O 1) Br 2 , HBr 2) (C 3 )COK O O 9 e) f) 1) NaO 2 ,HCl g) 1) LiAlH 4 NH 2 OEt O O OEt O 1) O , CH 32 ONa 2) H 3 O O O 2)KC 2) H 3 O 10 h) i) 1) KOH j) OEt O O OEt O 1) O , CH 32 ONa 2) H 3 O O O 2)PhC 2 Br 3) H 2 O, KH NH O O , heat