Adamson University Problem Set no.

5
Chemistry Department Organic Chemistry for Engineers

Alcohols, Ethers, Epoxides, Aromatic compounds, Aldehydes, Ketones, Carboxylic Acids, Amines

General Instruction: Write your answers on the space provided in this answer sheet. You may scan or
take a picture of your answer sheet and submit a soft copy (in MS word or PDF format) through
Blackboard.

I. Provide a systematic name for each of the following compounds:

No Structure IUPAC name

.
1 OH

2 OH

3 Cl

OH

Br
4 O

1
6 OH

7 OCH3

NO2

O
8

O2N
H

Br

O
10

Cl

2
 11 O Cl

HO OH

O
12 O

13 O

Cl

14 O

15 2,2,3,3-tetramethylhexan-1-amine

NH2

II. Draw the structure of the following compound given the IUPAC name.

No Structure IUPAC name

.
1

cis-1,2-Cyclohexanediol

2,4,6-Trinitrophenol

3
3 (R)-2,2-Dimethyl-3-heptanol

4 (S)-2-Methyl-1-butanol

5 2-Allyl-2-methoxyphenol

6 para-Xylene

7 ortho-Dichlorobenzene

8 meta-Chloroaniline

9 2,4,6-Tribromophenol

10 meta-Nitrotoluene

4
 11

(3R,4R)-3,4-Dihydroxypentanal

12 meta-Hydroxyacetophenone

13 4-Ethyl-2-propyloctanoic acid

14 cis-1,2-Cyclohexanedicarboxylic acid

15 N,2,2-Trimethylhexanamide

III. Draw the MAJOR product(s) of the following reaction.

1) O3
2) DMS
3) excess LAH
1.
4) H2O

5
 1) NaBH4, MeOH

O
2) TsCl, pyridine
3) NaSH
H
2.
1) Hg(OAc)2, H2O
2) NaBH4
3) Na2Cr2O7, H2SO4, H2O

3.
1) BH3•THF
2) H2O2, NaOH
3) PCC, CH2Cl2

4.
1) H3O+
2) concentrated H2SO4, heat

3) O3
4) DMS
5.

1) Hg(OAc)2, MeOH
2) NaBH4
6.
1) mCPBA

2) NaSH
3) H2O
7.

OH
1) NaH
2) O

3) H2O
8.

6
 OH
1) NaH
2) O

3) H2O
9.
O
1) H3O+

2) EtOH
10.

O Br O O

1) Cl , AlCl3
O O

2) Zn(Hg), HCl, heat

11.

conc. HNO3
conc. H2SO4
OCH3

12.

Fuming H2SO4

13.

HO
Cl

O2N AlCl3

14.

7
 O

Cl

N
H
AlCl3

15.

1) PhMgBr
O
2) H2O
16.

CH3CO3H

17.
H
N
CH3COCl
pyridine

18.
Br
1) NaCN, DMSO
2) excess LAH
3) H2O
19.

20.
1) HNO3, H2SO4
2) Fe, H3O+
3) NaNO2, HCl, < 5 deg C
4) CuCN

8
IV. Propose an efficient synthesis for each of the following transformations:

1.
O

O
H

2.

Cl H

O
3.
O

4.
O

HO

5.

6. OH O

OH O
OH

7.

9
 O

8.

9.

OH

OMe
10.

O2N

11.

Br

O 2N

12.

Cl Br

NO2
13.

10
 Cl NO2

O
14.
OH

CN

15.
O O

16.

OH

OH O

17.

SYNTHESIS:

O O

OH N
H

18.

11
 Cl O

NH2
NH2

Cl Cl
19.

NH2 N

20.

12