An ether solution contains the following components. ...

[RRMR]

An ether solution contains the following components.
 
   2,3,4,5-tetramethylbenzene benzyl alcohol 2-hydroxybenzoic acid
 
   If this solution is extracted with a 5 solution of NaHCO₃, that is immiscible with ether, which components end up in the ether layer and which in the NaHCO₃ layer?

Question 2

Instructions: Draw structures corresponding to each of the following IUPAC names.
 

Draw:
 
   phenylacetonitrile or phenylethanenitrile

Question 3

Instructions: Draw structures corresponding to each of the following IUPAC names.
 

Draw:
 
   prop-2-enenitrile

Question 4

Instructions: Draw structures corresponding to each of the following IUPAC names.
 

Draw:
 
   2-chlorobenzoic acid

Question 5

Instructions: Draw structures corresponding to each of the following IUPAC names.
 

Draw:
 
   cyanoacetic acid

Question 6

Instructions: Draw structures corresponding to each of the following IUPAC names.
 

Draw:
 
   cis-cyclopentane-1,3-dicarboxylic acid

Question 7

Instructions: Draw structures corresponding to each of the following IUPAC names.
 

Draw:
 
   2-propylpentanoic acid

Question 8

The two spectra below belong to acetic acid (ethanoic acid) and its isomer, methyl formate (methyl methanoate). Which spectrum corresponds to which compound? Explain your answer.
 
   
 
   
 
   (Spectra obtained from SDBSWeb: http://www.aist.go.jp/RIODB/SDBS)

Question 9

Draw the structure of the lactone product of the following reaction.
 
   

Question 10

The following a monomer of the polymer used in biodegradable sutures called Lactomer. Upon hydrolysis what product(s) form(s)? Draw the appropriate structure(s).
 
   

Question 11

Draw the structure of polymer formed in the following reaction. Show only a single monomer.
 
   

Question 12

Draw the structure of polymer formed in the following reaction. Show only a single monomer.
 
   

Question 13

Draw the major product of the following reaction (which affords a penicillin derivative).
 
   

Question 14

Draw the major products of the following biochemical reaction (where R = a fatty acid chain).
 
   

[tsternbergh47]

Answer to Question 1

Ether layer: 2,3,4,5-tetramethylbenzene and benzyl alcohol
NaHCO₃ layer: 2-hydroxybenzoic acid

Answer to Question 2



Answer to Question 3



Answer to Question 4



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Answer to Question 6



Answer to Question 7



Answer to Question 8

Both of these compounds contain two different kinds of protons. In addition, both of the protons in each compound are expected to appear as singlets. However, the position of the absorptions should be diagnostic.
The carboxylic acid proton in acetic acid should appear between 11 and 12  while the methyl singlet should appear between 2 and 3 , as in the bottom spectrum.

Answer to Question 9



Answer to Question 10



Answer to Question 11



Answer to Question 12



Answer to Question 13



Answer to Question 14



Answer to Question 15

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