Question

Question 1: Make a model of the bridged bicyclic compound, camphor, shown below:

a) Describe the bond orientation and structural features in terms of any strain.

b) How many stereoisomers are possible for this molecule?

c) Use models to help draw accurate 3D representation of any stereoisomers of camphor.

Question 2: Write out the equation for the reduction of camphor using sodium borohydride and use models to help draw the 3D structure of the products.

Question 3: Discuss the possible mechanisms for the formation of the 2 possible products of this reduction and predict which will predominate.

Question 4: The Haworth projections of the furanose and pyranose forms of D-glucose are shown below:

a) Make models of each and determine which is the most stable and what types of strain are involved to make other forms less favored.

b) Can you see how the lone pairs of the hemi-acetal ring oxygen are positioned to interact with the anti-bonding orbital of the sp³ hybrid of the other C-O of the hemi-acetal (i.e. the new OH group formed when the hemi-acetal is generated)? Point this out in your drawings.

ОШ .CH-ОН Онш CH-ОнН Не ОН Н O он Он ОН Он Cн-он CH-он Он о о Он Он Он Он ОН Он ОН or

Answer 1

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