32. (14) Predict the major organic product of the following reactions or provide the reagents needed to complete each transformation. Clearly show stereochemistry where appropriate. (a-b) (c-d) (e-f) (g-h) (i-j) (k-1) (m-n) KOH heat NBS hv 1. Br₂, light 2. CH3O+K, heat LDA heat CH3 NaBH4 CH3OH CH3 CH₂l2, Cu Zn H₂O CI H Br Na+ CN H₂O cold KMnO4 1. CH3MgBr 2. H₂O, H+ CH₂OH, heat CH3S +Na acetone mCPBA

7.26 Predict the principal organic product of each of the following reactions. Specify stereochemistry where appropriate. ONa (a) (b) (c) (d) (e) (1) (g) (h) e (j) L OH (1) H- Br + + OH OCH3 Br Br CoHs ONa NaOH NaN3 dioxane-water Ao fo X A Br NH3 methanol HCI CHC13 -CH3 CH,SNa -H OOH (k) CH₂(CH₂)₁6CH₂OTS + CH3CH₂CH₂CH₂SNa → CGHS CH₂ONa CH3OH 1. LIAIH, diethyl ether 2. H₂O K₂CO3 acetone

15.6 (pqr) Predict the major product or reagent that completes the transformation

None

7.43. A through C

Compound A, C,H160 is optically active and gives a negative results with Iodoform tuɔt and forms B, C,H14 when reacts with concentrated sulphuric acid. Ozonolysis of B forms C. C;H6O and D, C8H$O. Both C and D gives positive result with Iodoform test. Determine the structure of A, B, C and D and explain. 7.

(a) Provide the missing reagents and line structures of the products (C- E) for the following reactions. Include stereochemistry for products Cand E as indicated. No mechanisms are required. (5) C H,0 Show stereochemistry any one diastereomer OH PCC. CH;Cla D H. Pd/C Show stereochemistry any one enantlomer

(b) Provide retrosynthetic steps leading to ketone 9 from bicyclic compound 8. Provide all intermediates (synthons) and their equivalents clearly labelled. No synthetic steps and mechanisms are required. 8-1 NC. 8 9

Rank the following compounds

Draw the chemical structure for product (7) and provide a detailed (a) mechanism for the reaction [4] that explains the stereochemistry of product (8). (m-CPBA = meta-chloroperoxybenzoic acid) m-CPBA Он HCI C9H160 [4] (7) (8) [5] NaOH/H20 C9H1802