SCGS F.

7 AL Chemistry Assignment 4 CARBONYLS

1. Each of the following four carbonyl compounds reacts with hydrogen cyanide to give an addition product : CH3CH2CHO X CH3CHFCHO Y CH2FCH2CHO Z

(a) Using X as an example, write a mechanism for the reaction. (b) Arrange the three carbonyl compounds in increasing order of reactivity. Explain your order. 2. (a) In an experiment, 10.0 g of butanone reacts with 5.0 g of hydrogen cyanide to give 11.0 g of 2-hydroxy-2methylbutanenitrile. (i) Find the limiting reactant of the reaction, showing clearly your calculation. (ii) Calculate the percentage yield of 2-hydroxy-2-methylbutanenitrile. [Ans: 79.9%] (iii) Would the product rotate a beam of plane polarized light? Explain your answer. (b) Consider the five reactions of butanone, J, shown in the reaction scheme below:

(i)

Suggest a reagent by which K may be formed and give the structure for K.

(ii) Give the structures for compounds M and N. (iii) S is a structural isomer of J. S also reacts with 2,4-C6H3(NO2)2NHNH2 to give a red precipitate. Draw its structure. (iv) How may J and S be identified by making use of their reactions with 2,4-C6H3(NO2)2NHNH2 ? 3. From the following facts, write TWO possible structures for the organic compounds X and Y, giving reasons to support your deductions. State the relationship between the two possible structures in each case. Using only ONE of the possible formulae, write appropriate equation(s) to account for any observation. (a) X (C6H12O) is an achiral compound which effervesces rapidly upon addition of sodium metal, but does not affect by acidified potassium manganate(VII). (b) Y (C6H12O) is a chiral compound which gives an intense yellow precipitate with 2,4-dinitrophenylhydrazine in hydrochloric acid but does not react with Tollens reagent or acidified potassium dichromate. (c) Z (C6H12O) is a chiral compound which reacts with hydrogen in the presence of a palladium catalyst to give an achiral compound C6H14O. 4. 5. Using equations, indicate the reactions you would employ for the following conversions, which may involve more than one step. Give the reagent(s) for each step and the structure of any intermediate compound(s). (a)

(b)

(c)