Organic Chemistry Exam(B) Final 1.Fill blanks(20 points) (1)Write the IUPAC names for the following compounds. (a) Ethyl 4-oxo-hexanoate (b) (S)-2-Amino-N-ethyl-3-phenyl propanamide 2.6-Dibromophenol (S)-4-Ethyl-1,3-hexanedione (2)All naturally occurring monosaccharides possess D-configuration,whereas all naturally occurring optically active 2-amino acids possess L -configuration. (3)Draw the structures of (a)2-hlorofuran,(b)pyridine-4-carbaldehyde.()D-deoxyribose (Fischer Project) CHO H-H H-OH a H-OH (c)CH2OH (4)(a)Put EtOH,NH3.CHCOEt,and CH,COCHCOEt in the order of acidicity increase Acidicity increasing:NH3<CH COEt <EtOH<CH COCH-COzEt OHOH (5)The mechanism name for reaction of 4-chlorotoluene and sodium amide:Benzyne intermediate Mechanism OR Elimination and addition mechanism (6)Which compound is not aromatic? d
Organic Chemistry Exam (B) Final 1. Fill blanks (20 points) (1) Write the IUPAC names for the following compounds. O O (a) O ______Ethyl 4-oxo-hexanoate____ N H NH2 (b) O ______(S)-2-Amino-N-ethyl-3-phenyl propanamide OH Br Br (c) _ 2,6-Dibromophenol______ O O (d) __ (S)-4-Ethyl-1,3-hexanedione__ (2) All naturally occurring monosaccharides possess _D_-configuration, whereas all naturally occurring optically active 2-amino acids possess _L_-configuration. (3) Draw the structures of (a) 2-chlorofuran, (b) pyridine-4-carbaldehyde, (c) D-deoxyribose (Fischer Project). (a) (b) . (c) H H CHO H OH H OH CH2OH (4) (a) Put EtOH, NH3, CH3CO2Et, and CH3COCH2CO2Et in the order of acidicity increase. Acidicity increasing:_NH3 < CH3CO2Et < EtOH < CH3COCH2CO2Et _. (b) Draw the structure of a pentaose: _____________________________________________________________________ (5) The mechanism name for reaction of 4-chlorotoluene and sodium amide: __Benzyne intermediate Mechanism OR Elimination and addition mechanism___. (6) Which compound is not aromatic? ____d_________
oC①C 入NLif (7)The structure of LDAis (8)The structure of DMF is 2.Predict major products for following reactions,indicating stereochemistry if optional (30 points). 1)AICla 2)H30 HO人 AICls Zn(Hg).HCI △
(a) (b) (c) S (d) (e) + + - (7) The structure of LDA is (8) The structure of DMF is ___ ____________________. 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 Ph HO Ph
人0 6) (t)-cis-and(+)-trans (+)-cis-and (+-trans 9) OH 入入 + 0、又。20义
(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+ O O O O O O O N OH O OH O Br HO O O (+)-cis- and (+)-trans (+) (+)-cis- and (+)-trans (+)
又w人 H (12) N，30o NH COOH (13)入 (14) +CHNH2+F0△→ =0 (15) Me NaNO2.HCI CucI Me MeO〈》-NH2 3.Identify structures on the basis of provided spectral data and reaction(s)(15 points). (1)Compound(A):Molecular formula:CsHo.ItsH NMR spectrum is as following (2)In acidic methanol,3-oxobutanal is transformed into a compound(B)with the molecular formula CHO.Its'H NMR and IR spectral data:'H NMR 8(ppm):2.19(s,3H),2.75 (d,2H). 3.38(s,6,4.89(t1 H)and IRv(cm1715. (3)Compound(C):CsHO,Its 'H NMR spectrum as following 2H Predict their structures
(11) (12) (13) (14) (15) O O Me2CHNH2, MeOH O O O NH3, 300oC 1) NaOH, Br2 2) H3O+ N 1) MeI 2) Ag2O, H2O O O + CH3NH2 + O Me MeO NH2 NaNO2, HCl CuCl NH O O COOH NH2 N O Me MeO Cl OH O NH 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
4.Write reasonable and stepwise mechanisms for the following reactions(15points). (1) NO2 NO2 oN--a·EoNa一oN-oa+a "CCo 00
(A) (B) (C) O 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)
Mechanism 4一8 的-心- 好
O O O O O O OH O OH Mechanism:
5.Synthesize the following compounds with oranic starting materials with onlyne function group and no more tnan o carbon atoms,and other inorganic reagents(20 points). (1) (2 0品
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) Answer: (1) Cl O AlCl3 O H2SO4 O SO3H (2) H2SO4 SO3H Fe, Br2 SO3H Br Br H+ Br Br KMnO4 CO2H Br Br (3) (4) O O O O O OEt O O BnBr OEt O O Ph n-PrBr OEt O O Ph 1) NaOH 2) H+ 3) Δ O O O O Br O O MeI OHH2O EtONa EtONa EtONa EtONa