SCGS F.

7 AL Chemistry Assignment 2 - HALOALKANES

1. 1-chloropropane reacts with potassium hydroxide in an SN2 manner to give propan-1-ol. (a) Using curly arrows to indicate electron pair displacement, outline a mechanism of the reaction. (b) Draw a labelled energy profile for the reaction. (c) Explain the expected change in reactivity when 1-chloropropane is replaced by (i) 1-iodoproane; (ii) 2-chloropropane ? From the following facts and observations, write ALL possible structures for the organic compounds X and Y, giving reasons to support your deductions. Write appropriate equation(s) to account for any observation. (a) X is an hydrocarbon of molecular formula C7H14 which does not decolorize aqueous bromine. Upon chlorination in sunlight, it gives rise to a maximum of 4 possible mono-substituted products. (b) Y, with molecular formula of C4H7Cl, is an acyclic compound which decolorizes potassium permanganate solution. 3. Identify the mechanisms for the following reactions using the combination of these terms: substitution, addition, elimination, electrophilic, free radical and nucleophilic. Also give the suitable reagent(s) and/or condition(s) for each reaction. (a) CH3CH2CH2OH (b) CH3CH=CH2 (c) CH3CH=CH2 (d) CH3CH=CH2 4. Identify A, B, C and D in the following reactions: (a) CH3CH(OH)CH3 (c) C 5. O3 PBr3 A (b) B Br2(aq) D (CH3)2CHCH2OCH3 CH3CH2CH2Br CH2BrCH=CH2 CH3CHBrCH3

2.

CH3CO(CH2)4CHO

(d) (CH3)2CHCH2I

Give the structures of the major organic products, G and H, in (i) and (ii) below. Outline a mechanism for the formation of the major product in each of the three reactions.

6.

Suggest a chemical test to distinguish one compound from the other in each of the following pairs. Your answer should include the reagents and/or conditions used and the observation expected for each test. (a) CH3CH2CH2Cl (b) CH2=CHCH2Br AND AND CH2=CHCH2Cl CH2=CHCH2I

7.

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) CH3CH2CH2Br (b) (c) (CH3)2CHOCH3