Spring 2017 NEPHAR109 Organic Chemistry I

Problem Set 2, Assist.Prof. Banu Keşanlı

1. Give the major product of the following chemical reactions.

H2SO4
Δ
OH

Pd
+ 1 mol H2

H3 C
NaI
Br
acetone
HO
H
R- configuration of product ?

HC CCH2CH2CH3 + HI

2. Give the products for each of the chemical transformation.

(a) H2 /Pd
(b) Br2
(c) HBr
CH3CH=CH2 +
(d) H2O, H3 O+
(e) KMnO4, OH-, H3O+, heat

3. What product would form from each of these reactions with the given alkyne.

CH3 (a) 1 equiv. Br2

(b) 2 equiv. H2 Pd/C
CH3CHCH2CH2C CH + (c) 1 equiv. HBr, ROOR
(d) KMnO4, heat

4. Give the products of the reactions shown below.

MnO4-
(a)
H3 C CH3
OH-, cold
HC C
MnO4 -, OH-
CH3 (b)
H3O+, heat
1
5. Draw the structures of the following compounds.

(a) 3,3-Dimethyl-4-octyne (b) Z-3-methyl-2-pentene

(c) 3-fluoro-1-pentyn (d) trans-2-butene

6. Name the following compounds.

CH3 CH3
Br CH3CH2 CH2CH2F
CH3 CH2CC CCHCH3
CH3 H H

F
H 3C CH2 CH3

Br H H3CC CCH2CHClCH3

7. Suggest the structures of alkenes that give the following reaction products.
CH3
HCl
? CH3CHCHCH2 CH2CH2CH3
Cl

OH
cold KMnO4
?

OH

8. Indicate reagents needed to be used for the following chemical transformations.

CH3 ? O
H3 C O
+
CH3 CH=CHCHCH3
H3C CH
H3C OH OH

CH3
CH3 ?
CH3 C=CH2 CH3CHCH2OH

2
 ?
CH2=CHCH3 CH3CH2CH3

9. True or False

10. (a) Ibuprofen is a popular analgesic and anti-inflammatory drug and exists in
enantiomeric form. Choose the incorrect statement about ibuprofen and its enantiomer.

A) The molecular weights of both enantiomers are the same.

B) The melting points of both enantiomers are the same.
C) The toxicity of the two enantiomers must be equal.
D) The color of the two enantiomers must be the same.

11. Assign (R) or (S) configuration. Draw the enantiomer of molecule (a).
(a)
F
H 3C Br
OH
Cl C2 H 5
CH3 H

(b) Are these two the same or enantiomers?

NH2 COOH

COOH H
H H2N
CH3 CH3

12. How many stereogenic carbon centers does ephedrine have? Show on the molecule.
OH

CH3

NH
H3 C