Chemistrystudents.leeds.ac.uk

Year: 2013-14
Name:
1. AMANTADINE (MChem only)

(i) N-(1-Adamantyl)acetamide
Phys App
(5) NMR(spec)
(15) NMR(assign)
Mechanism

(ii) Amantadine
Phys App
(10) NMR(spec)
(5) NMR(assign)
Mechanism
(10) Questions (3)

2. CHIRAL EPOXIDATION
(i) (3S,4R)-2,2-Dimethyl-3,4-epoxy-6-pentafluoroethyl-2H-1-benzopyran
Phys App.
(20) NMR(spec)
(10) NMR(assign)
(10) [α]D
Mechanism
Year: 2013-14
Name:

(ii) (3S,4R)-2,2-Dimethyl-4-(2-oxopiperidin-1-yl)-6-pentafluoroethyl-2H-1-benzopyran-3-ol
Phys App.
(15) NMR(spec)
(15) NMR(assign)
(5) [α]D
(10) Questions (4)
Mechanism

3. IBUPROFEN
(i) 4-Isobutylisopropenylbenzene
Phys App
(15) NMR(spec)
(15) NMR(assign)
Mechanism

(ii)(S)-2-(4-Isobutylphenyl)-1,2-diol
Phys App
(15) NMR(spec)
(5) NMR(assign)
Mechanism
Year: 2013-14
Name:

(iii)(S)-2-(4-Isobutylphenyl)-propanol
Phys App
(15) NMR(spec)
(10) NMR(assign)
Mechanism

(iv) (S)-Ibuprofen
Phys App
(15) NMR(spec)
(5) NMR(assign)
(10) [α]D
Mechanism
(10) Questions (3)

4. NITRAZEPAM
(i) 1-Bromoacetamido-5-nitrobenzophenone
Phys App
(5) NMR(spec)
(10) NMR(assign)
Mechanism
Year: 2013-14
Name:

(ii) 2-Azidoacetamido-5-nitrobenzophenone
Phys App
(15) NMR(spec)
(5) NMR(assign)
Mechanism

(iii) Nitrazepam
Phys App
(10) NMR(spec)
(5) NMR(assign)
Mechanism
(10) Questions

(iv) Rationalisation of the NMR using molecular modelling
Modelling exercise
Year: 2013-14
Name:

5. FLUOXETINE
(i)R-(+)-3-Chloro-1-phenylpropan-1-ol
Phys App
(15) NMR(spec)
(5) NMR(assign)
(10) [α]D
Mechanism

(ii) R-(-)-3-Iodo-1-phenylpropan-1-ol
Phys App
(15) NMR(spec)
(15) NMR(assign)
(15) [α]D
Mechanism

(iii) R-(-)-3-N-Methylamino-1-phenylpropan-1-ol
Phys App
(15) NMR(spec)
(15) NMR(assign)
Mechanism
Year: 2013-14
Name:

(iv) a. R-(+)-Fluoxetine, (v) b. R-(+)-Fluoxetine hydrochloride
Phys App
(10+10) IR (b)
(10+10) NMR(spec)
(5) NMR(assign)
(10) Questions (2)
Mechanism
(5) [α]D

6. PROPRANOLOL (MChem only)
(i) (2R)-Glycidyl tosylate
Phys App
(15) NMR(spec)
(5) NMR(assign)
Mechanism

(ii) (2R)-Glycidyl naphthyl ether
Phys App
(15) NMR(spec)
(15) NMR(assign)
Mechanism
Year: 2013-14
Name:

(iii) (2S)-Propranolol
Phys App
(15) NMR(spec)
(15) NMR(assign)
Mechanism

(iv) (2S)-Propranolol hydrochloride
Phys App
(15) NMR(spec)
(5) NMR(assign)
(10) [α]D
Mechanism
(10) Questions (2)

ANALYTICAL EXERCISES

COMMENTS (Illness, absences, etc.)

Source: http://www.chemistrystudents.leeds.ac.uk/fileadmin/user_upload/Current__Students/MEDICINAL_CHEMISTRY_level_3_mark_sheet_blank.pdf