1B Carbonyls    /23

   

    1)          Draw the displayed formula for 2 - methyl pentanal  [1]

 

                                                                

 

    2)          State and explain the bonding in the carbonyl group.  You may wish to include a diagram:  [3]       

                              

                                                diagram and p orbitals labelled  [1]

                                                diagram and p orbitals labelled  [1]

                                                p orbitals overlap forming p orbitals  [1]

                                            

    3)          Name and draw the structure of the product(s) formed when 2 methyl propanoic acid is treated with NaBH4:  [4]

 

  2 methyl propanal (shown) [1]  drawn  [1]

2 methyl propan - 2 - ol  [1]  drawn  [1]

 

    4)          Complete the mechanism for the reduction of this aldehyde:  [6]

 

Dipole on carbonyl [1] 

Curly arrow from LP on hydride to the d+ carbon in the carbonyl [1]

Curly arrow from middle of the C=O bond to the O [1]

Correct intermediate drawn [1]

Curly arrow from the LP on the O to the d+ H in water [1]

Curly arrow from the middle of the H - O bond in water to the O in water [1]

 

 

    5)          Describe a simple chemical test to distinguish between an aldehyde and a ketone:  [4]

 

  Add sodium dichromate [1] and sulphuric acid  [1]

Orange to green with aldehyde  [1] 

No change with a ketone  [1]

 

Add silver nitrate [1] dissolved in ammonia  [1]

Silver mirror / precipiatate with aldehyde  [1] 

No change with a ketone  [1]

 

    6)          Outline a chemical process to determine which aldehyde or ketone you have:  [5]

 

  Add 2,4,DNPH [1] you get orange crystals  [1]

Filter, recrystalise, filter and dry  [1] 

Carry out a melting point determination  [1]

Compare melting point with known data  [1]