Question

Starting from 3-methylhex-1-ene as the substrate at the center of your page, draw a reaction map showing the regiochemical and stereochemical outcome or outcomes for each of the following series of reagents. Name each of your products, including stereochemical designations for any chirality centers that are generated.

**Pay attention to the possibility of rearrangement when your mechanism produces a carbocation.

 A. H₂SO₄, H₂O

B. 1. Hg(OAc)₂, H₂O; 2. NaBH₄

C. 1. BH₃•THF; 2. H₂O₂, NaOH

D. Br₂, CCl₄

E. Br₂, H2O

F. HBr

G. HBr, ROOR

H. 1. O_3; 2. DMS
I. H₂, Pt

Answer 1

OH H₂ SOG inoy tho Hydration Reachicos C) -3-methyl hexan-3-01 (S)-3-methyl- hexan-3-01 (0) 1. Hg (OAC)2, tho 2 Nabha Ciezwabon- Denierucabon Reaction wf+wy or (C) 1. Bl. THE 214502-NaOH Hedccbocahoo- crajdabico reachicos OH OH (2R)-3 mmethyl hexan-2-01 2S)-3-methyl- hoh hexan-2-01 3-methyl hexan-1-01 -) Biz Myo ambayo •Brt -B.6 OH (0) cola Brommabon Reachca BY (28)-1, 2 dibromo-3-methyl (PR)-1,2-dibomo-3- hexane methyl hexane Brz (E) tho Halohydoin bormaticos (23)-f-bromo-3-methyl hexan-201 OH (2R) HBY BC (F) Hydrobcominanco (R)-3-bromo-3-methyl (S)-3-66060-3-methyl- hexane -Br 1-bromo-3-methylhexane 1.03 H + H Hih 2inms Occolysis Formaldehyde 2-methyl Propanal thipt 1111Br + HB6 hexane ROOR CHU ( 1 ) Hydrogenation 3-methyl hexane