Question

Question 29: Complete the boxes, drawing out the stereochemistry when appropriate. Include the full mechanism with arrows to show movement of electrons. For each A, B, C, determine if the final product is racemic, and if appropriate, draw the most stable chair conformer. BH HCI (conc) A 1-isopropyleyclohex-l-ene H4O2, NaOH B (15,25,3R)-1-chloro-2,3-dimethylcyclohexane SH ОН с (18,3R)-1-iodo-1,3-dimethylcyclohexane

Answer 1

The first reaction is sn1 reaction with rearrangement forms 1chloro 1 isopropyl xyclohexane.

2,3rd reactions are sn 2 reactions

Bolly a 12 co • Bb Naon on Conc. Mol ell 2) نم си, Mercus TSH tc\/ (15,25, 3R) 1-chloro (SN?) 2,3 dimethyl Cyclohexane 3 cllz s 1 Ch R oper era 3) Ech Ch (SNP) ( IS, 3R) 1-Iodo 4,3 dimethyl cyclohexane IO R but s due to I (farther alway) from observer - Cub s but R (due to lowest priority of the op