CM1121: Organic Chemistry 1

Mass Tutorial 1

Chapters 5, 6, 8 , 9, 10 and 11

Q1. Draw the major organic products for the following reactions (if there are several enantiomers

or diastereomers formed, show only one, but pay attention to stereochemistry where needed). Aqueous

workup is implied after each step where needed.

(i) (CM1121, Exam 2016, Question 1g)

(ii) (CM1121, Exam 2014, Question 1a)

(iii) (CM1121, Exam 2013, Question 1b)

(iv) (CM1121, Exam 2013, Question 1f)

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 CM1121: Organic Chemistry 1

ANSWERS
Chapters 5, 6, 8 , 9, 10 and 11

Q1

(i)

(ii)

(iii)

(iv)

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 CM1121: Organic Chemistry 1

Mass Tutorial 2 and 3

Chapters 14 and 16

Q2A (CM1121, Exam 2016, Question 3)

Lovastatin, a naturally occurring compound (initially isolated from the fungus Aspergillus terreus) was

the first statin drug approved by the FDA for treatment of high LDL cholesterol. Like many natural

products, the biosynthetic pathway leads to a single stereoisomer.

(i) How many stereogenic centres are there in lovastatin ?

(ii) Draw the structure of lovastatin clearly in the answer booklet and assign the absolute

configuration (R or S) of every stereogenic centre [Note: Unclear/ ambiguous assignments will be

considered incorrect].

Q2B (CM1121, Exam 2015, Question 3)

Sulopenem, a penem antibiotic, shows potent antibactericidal activities against both Gram-positive and

Gram-negative bacteria.

(i) How many stereogenic centres are there in sulopenem ?

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 CM1121: Organic Chemistry 1

(ii) Draw the structure of sulopenem clearly in the answer booklet and assign the absolute

configuration (R or S) of every stereogenic centre [Note: Unclear/ ambiguous assignments will be

considered incorrect].

Sulopenem

ANSWERS
Chapters 14 and 16

Q2A

(i) 8 stereogenic centres

(ii)

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 CM1121: Organic Chemistry 1

Q2B

(i) 6 stereogenic centres

(ii)

Sulopenem

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