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Mid Examination of

This document provides a 90-minute examination on basic drug synthesis concepts. It contains 5 questions asking students to outline syntheses of various organic compounds through nucleophilic substitution, addition, oxidation, and retrosynthetic analysis reactions starting from common organic building blocks like benzene, aniline, 1-propanol, butanal, and cyclohexanol. Students are asked to provide structures and IUPAC names for intermediate and final products. The examination tests students' ability to develop multi-step synthesis routes utilizing common named reactions and retrosynthetic analysis.

Uploaded by

Kurnia Tri Wijaya
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Download as DOCX, PDF, TXT or read online on Scribd
60 views

Mid Examination of

This document provides a 90-minute examination on basic drug synthesis concepts. It contains 5 questions asking students to outline syntheses of various organic compounds through nucleophilic substitution, addition, oxidation, and retrosynthetic analysis reactions starting from common organic building blocks like benzene, aniline, 1-propanol, butanal, and cyclohexanol. Students are asked to provide structures and IUPAC names for intermediate and final products. The examination tests students' ability to develop multi-step synthesis routes utilizing common named reactions and retrosynthetic analysis.

Uploaded by

Kurnia Tri Wijaya
Copyright
© © All Rights Reserved
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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MID EXAMINATION OF

BASIC OF DRUG SYNTHESIS

Time: 90 minutes April, 15, 2010

1. Show how you might use a nucleophilic substitution reaction of 1-bromopropane to


synthesize each of the following compounds:
OH O SH
a. b. 1-iodopropane c. d.

2. Give the structures and acceptable names for the compounds that would be formed when
1-pentanol is treated with each of the following reagents:
a. Phosphorus tribromide (PBr3) c. Sodium hydride (NaH)
b. Thionyl chloride (SOCl2) d. HBr (conc.), reflux.

3. Write structural formulas for the products that form when 2-methyl-2-butene reacts with
each of the following reagents:
a. HCl c. dilute H2SO4, warm d. Cold concentrated H2SO4
b. Cold concentrated H2SO4, then H2O and heat

4. Starting with the appropriate sulfonic acid and PCl5, or with the appropriate sulfonyl
chloride, show how you would prepare:
a. ethyl p-toluenesulfonate
b. tert-butyl methanesulfonate

5. Starting with ethyne and using retrosynthetic analysis, out line a synthesis of 1-pentyne.

--- Good Luck ---


FINAL EXAMINATION OF
BASIC OF DRUG SYNTHESIS

Time: 90 minutes June, 07, 2010

1. Starting with benzene, out line a synthesis of each of the following:


a. Propylbenzene
b. m-bromonitrobenzene
c. p-chlorobenzenesulphonic acid

2. a. Starting of aniline and assuming that you have 2-aminothiazole available, show how
you would synthesize sulfathiazole.
c. How would you convert sulfathiazole to succinylsulfathiazole?

O O
NH2 NHCCH2CH2COH

H2N S SO2NH SO2NH


S S
N N N
2-aminothiazole sulfathiazole succinysulfalthiazole

3. With 1-propanol as your only organic starting compound, out line a synthesis of 4-
heptanone.

4. Show how each of the following products could be synthesized from butanal:
a. 2-ethyl-2-hexen-1-ol b. 2-ethyl hexanal

5. Give structures for compounds A-D:


H2CrO4 1. CH3MgI H2SO4
Cyclohexanol A (C6H10O) B (C7H14O) C (C7H12)
Acetone 2. H3O+ heat
1.O3
2.Zn,HOAc

D (C7H12O2)

--- Good Luck ---

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