NJC Organic Chem Structured revision set

Organic Chemistry Revision Booklet (Structured Qn) 2024 National Junior College 1 Name: _____________________ Class: _____________ Organic Chemistry Revision Booklet (Structured Questions) Content Page 1 Organic Synthesis 2-35 2 Distinguishing Test 36-42 3 Reaction Mechanism 43-54 4 Amino acid and Proteins 55-59 5 Kinetics of Organic Chemistry 60-63 6 Acidity and Basicity of Organic Compounds 64-67 7 Isomerism 68-69 8 Organic Structural Elucidation 70-83

Organic Chemistry Revision Booklet (Structured Qn) 2024 National Junior College 2 1) Organic Synthesis 1 The diagram below shows the synthetic pathway by which compound F may be prepared. The inorganic side product, which is produced together with compound F, is constantly removed from the reaction mixture. O2N Cl CH3 CH3 NH2 Cl CH3 CH3 NH2 OH CH3 CH3 C6H9OCl C6H9O2Cl A B C D E NH2 O CH3 O Cl CH3 F Step 1 Step 2 Step 3 (a) Give the structural formulae for compounds D and E. (b) Suggest the reagents and conditions for steps 2 and 3. (c) Draw the structures of the organic products formed when compound F is reacted with each of the following: (i) Br2(aq) (ii) KOH(aq), heat under reflux

Organic Chemistry Revision Booklet (Structured Qn) 2024 National Junior College 3 2 The reaction scheme below shows the final stages in the synthesis of compound S. Cl COOH Cl CH2CH2OH R Q P S Cl NH O OH Cl s (a) Draw the displayed formulae of compounds R and Q. (b) Give the synthetic route, involving not more than three steps, from P to Q. In your answer, suggest the reagent(s) and conditions involved in each step and draw the structural formulae of the intermediate organic products. Name the type of reaction occurring at each step. (c) In the reaction of R and Q, another organic compound can also possibly be formed. Draw the structural formula of the organic compound and explain how its formation may arise.

Organic Chemistry Revision Booklet (Structured Qn) 2024 National Junior College 4 3 There are four stereoisomers of compound P. P (a) What is the type of stereoisomerism exhibited by P? Draw the stereoisomers of P. (b) Q is a structural isomer of P in (a). Suggest the structures of Q, R, S, T and U in the reaction scheme below. Q (C11H12O2) aqueous HCl heat R (C3H6O2) + S U (C8H7OBr3) aqueous bromine T CH OH CHCH2CH CHOH H2 /Ni catalyst; heat

Organic Chemistry Revision Booklet (Structured Qn) 2024 National Junior College 5 4 O OH CH2NH2 CH2C N C O CH2CH3C O CH3 H Q (i) Name the four functional groups in compound Q, other than the phenyl group. (ii) Draw the structural formulae of the compound(s) when compound Q is treated with o Cold HCl(aq) o Hot NaOH(aq) o 5 1-bromo-2-methylpropane undergoes a series of reactions as shown by the given flow scheme. (i)