Organic Chemistry Exam(B) Final 1.Fill blanks(20points) (1)Write the IUPAC names for the following compounds. b (2)All naturally occurring monosaccharides possess -configuration,whereas all -configuration (3)Drav (Fischer Project). (6 fe) (4)Put EOH,NH CHCOEt,and CH,COCHCOEt in the order of acidicity inerease Acidicity increasing (5)Draw the structure ofa pentaose: (6)The mechanism name for reaction of 4-chlorotoluene and sodium ( ○个① (8)The structure of LDAis (9)The structure of DMF is
Organic Chemistry Exam (B) Final 1. Fill blanks (20 points) (1) Write the IUPAC names for the following compounds. O O (a) O _____________________________ N H NH2 (b) O _____________________________ OH Br Br (c) ______________________________ O O (d) ______________________________ (2) All naturally occurring monosaccharides possess ____-configuration, whereas all naturally occurring optically active 2-amino acids possess ____-configuration. (3) Draw the structures of (a) 2-chlorofuran, (b) pyridine-4-carbaldehyde, (c) D-deoxyribose (Fischer Project). (a) (b) (c) (4) Put EtOH, NH3, CH3CO2Et, and CH3COCH2CO2Et in the order of acidicity increase. Acidicity increasing:____________________________________________________. (5) Draw the structure of a pentaose: _______________________________________________________________________ (6) The mechanism name for reaction of 4-chlorotoluene and sodium amide:____________________. (7) Which compound is not aromatic? _____________. (a) (b) (c) S (d) (e) + + - (8) The structure of LDA is ________________________. (9) The structure of DMF is _______________________
2.Predict major products for following reactions,indicating stereochemistry if optional (30 points). "·A8 AICls Zn(Hg),HCI △ Hao' 'PPh3 X BuLi CHgCOsH OH TsOH.PhH NaOH 8 TsOH.PhH (9) Br2.trace P OH (10) 2 EtMgBr HaO*
2. Predict major products for following reactions, indicating stereochemistry if optional (30 points). O + (1) 1) AlCl3 2) H3O+ (2) Cl O + AlCl3 Zn(Hg), HCl (3) (4) (5) (6) (7) (8) (9) (10) C-Li + O I O H3O+ + PPh3 XBuLi O O CH3CO3H O + HO OH TsOH, PhH O O NaOH O H N TsOH, PhH O O H3O+ OH O Br2, trace P O O 2 EtMgBr H3O+
(12) 1)NaOH,Br2 2)H30° 2g.o.Hao △ (14)=0 +CHNH2+厂O△ (15)Me Meo--NH NaNO2.HCI CuCI 3.Identify structureson the basis of provided spectral dataand reaction(s)(15points) (1)Compound (A):Molecular formula:CH Its H NMR spectrum is as following (2)In acidic methanol,3-oxobutanal is transformed into a compound(B)with the molecular formula.Its 'H NMR and IR spectral data:H NMR(ppm):2.19(s,3H),2.75(d,2H). 3.38(s,6H),4.89(L,1H)and IRv(cm1715. (3)Compound(C):CsHO,Its 'H NMR spectrum as following. 3H Predict their structures (A) (B)
(11) (12) (13) (14) (15) O O Me2CHNH2, MeOH O O O NH3, 300o C 1) NaOH, Br2 2) H3O+ N 1) MeI 2) Ag2O, H2O O O + CH3NH2 + O Me MeO NH2 NaNO2, HCl CuCl 3. Identify structures on the basis of provided spectral data and reaction(s) (15 points). (1) Compound (A): Molecular formula: C8H10. Its 1 H NMR spectrum is as following. 8 7 6 5 4 3 2 1 0 PPM (2) In acidic methanol, 3-oxobutanal is transformed into a compound (B) with the molecular formula C6H12O3. Its 1 H NMR and IR spectral data: 1 H NMR δ (ppm): 2.19 (s, 3H), 2.75 (d, 2H), 3.38 (s, 6H), 4.89 (t, 1H) and IR v (cm-1): 1715. (3) Compound (C): C5H10O, Its 1 H NMR spectrum as following. 3 2 1 0 PPM 2H 2H 3H 3H Predict their structures (A) (B) (C)
4.Write reasonable and stepwise mechanisms for the following reactions(15 points) 1 NO2 NO2
4. Write reasonable and stepwise mechanisms for the following reactions (15 points). O2N NO2 Cl + EtONa O2N NO2 OEt + NaCl (1) O O OH H+ 100 oC O (2) O O OH OH + (3)
5.Synthesize the following compounds with organic starting materials with only one functional group and no more than6 carbo n atoms.and oher reagents (20 points)
5. Synthesize the following compounds with organic starting materials with only one functional group and no more than 6 carbon atoms, and other inorganic reagents (20 points). O O O CO2H Br Br O SO3H (1) (2) (3) (4)