Unit 1B: Carbonyl compounds test 1) /30      2) Propanal, CH3CH2CHO, can be used in the synthesis of organic compounds. CH3CH2CHO reacts with NaBH4 in a nucleophilic addition reaction. The nucleophile can be represented as a hydride ion, H–. A mechanism for the reaction is shown below. H + H NaBH4 step 1 C H H (i) O – O– O CH3C H2 + CH3CH2 C H step 2 H organic product – Add 'curly arrows' to the mechanism to show how the intermediate reacts with the water molecule in step 2.  (ii) Draw the structure of the organic product in the box above.  (iii) What is meant by the term nucleophile?  (iv) 3) Describe, in words, exactly what is happening to the electron pairs and bonds in step 1 of the mechanism above.  Glyceryl trihexanoate is a triglyceride that can be made from glycerol (propane-1,2,3-triol) and hexanoic acid, C5H11COOH. a) Draw the structure of glyceryl trihexanoate. Show every bond in the functional groups.  b) Naturally occurring glyceryl tritrihexanoate is found in vegetable oil. It can be used to produce biodiesel using transesterification. Write a chemical equation outlining the reaction, giving all reagents necessary.  4) As a wine ages, some of the carboxylic acids slowly react with ethanol in the wine to produce esters. (i) Draw a displayed formula to show the structure of the ester formed when propanoic acid reacts with ethanol.  (ii) Suggest what effect this process might have on the flavour of the wine. Explain your reasoning.  5) Compound A is used to add the flavour of mushrooms to foods. O C H 3C C H CH2 O C CH3 compound A (a) (i) Apart from the benzene ring, name the two functional groups in compound A.  (ii) Draw the skeletal formula of compound A.  (iii) Deduce the molecular formula of compound A.  (b) If the food is cooked for a long time, naturally occurring acids catalyse the hydrolysis of compound A. Draw structures to show the two organic compounds formed by the acid hydrolysis of compound A.