organic chemistry

Homework One – version A

Do this version if your last name starts with A-K

 

Question 1 – this question is related to spectrum A below.

Draw a dash-wedge structure of this molecule that meets the following requirements – (1) it has 2 consecutive asymmetric carbons  (2) you use Newman projections in your conformational analysis.

(a) Name this molecule (if you include stereochemistry you will get extra credit!)

(b) Show a Newman projection that is an exact representation of the conformer of your dash-wedge structure.  Label this Newman projection (i.e. C3-C4 or C2-C1).

Now rotate this molecule to give all the possible conformers.  Think about the stability of each relative to one another.

(c) Draw most stable conformer in all possible available diagrams (Newman, Fischer, dash-wedge)

(d) Draw the second least stable conformer (ranked as 5) in all possible available diagrams (Newman, Fischer, dash-wedge).

(e) Draw the enantiomer of your original dash-wedge structure.

(f) Explain why your enantiomer is equally as stable using 20 words or less.

 

 

 

Spectrum A: C6H10O

 

 

 

Question 2 – this question is related to spectrum B below

Draw a dash-wedge structure of this molecule that meets the following requirements – (1) it has 2 asymmetric carbons (2) you use chair diagrams in your conformational analysis.

(a) Draw both conformers of your molecule.

(b) Circle the more stable conformer of the ones you drew.

(c) State whether it’s diastereomer will be more or less stable, and explain this in 20 words or less.

 

Spectrum B: C8H17N

 

 

 

 

 
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