學號：

8. Give IUPAC names for the following

姓名： compounds:
1. Calculate the degree of unsaturation in the
following formulas:
(a) C10H12N2O3 (b) C6H9Br (c) C4H5NO
2. Draw sturctures for the following compounds: 9. Place asterisks at all chirality centers in the
(a) (4E)-2,4-Dimethyl-hexa-1,4-diene following molecules:
(b) (3E,5Z)-2,6-Dimethyl-octa-1,3,5,7-tetraene
(c) (2R,3S)-Dibromooctane
(d) (S)- Butan-2-ol
(e) Hepta-3,5-dien-1-yne
3. Assign Cahn-Ingold-Prelog priorities to the 10. Predict the products from reaction of
following sets of substituents: hex-3-yne with the following reagents:
(a) -C≡CH, -CH＝CH2 , -COOH, -C6H5 (a) H2,Lindlar catlyst (b) O3, followed by Zn,
(b) –CN, CH2Br, -Br, -CH2CH2Br CH3COOH (c)H2O,H2SO4,HgSO4
4. Assign R or S configurations to the chirality 11. Explain and give an example for the following
center in the following molecules: items:
(a). Markovnikov rule (b). Racemic mixtures
(c) Oxymercuration-reduction
(d). Tautomers (e) enatiomers
12. Using the curved arrows to indicate the
mechanisms of the following reactions and its
5. A 2.0 g sample was dissolved in the 5mL solvent, products.
then placed in a sample cell with 5.0 cm
pathlength. The observed rotation at the sodium
D line was +2.42。. Calculate [α]D for the sample.
6. How would you sythesize the following
compounds from C2H2 and any alkylhalides(RX)
with four or fewer carbons? More than one step
may be required. 13.Fill the blank (a)-(e) of the following：
(a) cis-3-pentene (b) CH3(CH2)4CHO
(c)CH3CH2COCH2CH2CH3
7. Predict the products of the following reactions:

14.An unknown compound A(C7H14) reacts with

1molar equivalent of H2. A also reacts with OsO4 to
give diol B. When reacts with KMnO4 in acidic
solution, A give two fragments. One is
CH3CH2COOH, and the other is a ketone C. Write
the reactions and structures of A, B and C.