12 - Chem 10172, Spring 2008 (1) (a) PROBLEM SET 12...

Info iconThis preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
Chem 10172, Spring 2008 PROBLEM SET 12 SOLUTIONS Due Tuesday, April 22 1 (1) (a) HBr Br (b) Cl 2 CCl 4 Cl Cl (and enantiomer) (c) H 3 O + H 2 O OH (and enantiomer) (d) 1) BH 3 2) H 2 O 2 , OH OH (e) O 1) BH 3 2) H 2 O 2 , OH O OH (and enantiomer) (f) O HO cat. H 2 SO 4 O O (g) 1) BH 3 2) H 2 O 2 , OH OH (racemic, but the other diastereomer is not formed) (h) Br 2 H 2 O OH Br (racemic, but the other diastereomer is not formed) (2) (a) H O H H H O H H (b) H Br H Br Br
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Chem 10172, Spring 2008 PROBLEM SET 12 SOLUTIONS Due Tuesday, April 22 2 (c) O H O H H O H H O H H O H H O H H O H H O H O H O H H In (c), it doesn’t matter which alkene reacts first. (d) OH Br Br OH Br CH 3 Br O H N CH 3 Br O Note the anti stereochemistry of the addition of the Br and ROH group to the alkene. The pyridine is too weak a base to deprotonate the alcohol until after it cyclizes. (e) 1) Br 2 , H 2 O O Br Br Br O H H O Br H H O H H O Br H O Br H 2) O–H O Br O
Background image of page 2
Chem 10172, Spring 2008 PROBLEM SET 12
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Image of page 4
This is the end of the preview. Sign up to access the rest of the document.

Page1 / 4

12 - Chem 10172, Spring 2008 (1) (a) PROBLEM SET 12...

This preview shows document pages 1 - 4. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online