Solutions_Manual_for_Organic_Chemistry_6th_Ed 317

Solutions_Manual_for_Organic_Chemistry_6th_Ed 317 - 1 4-33...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: 1 4-33 continued HO (j ) ( k) � H o ( I) � Br OH (n) CH3 ry."OCH3 �1 I 0H (a) On long-term exposure to air , ethers form peroxides. Pero xides are explosive when concentrated or heated. (For exactly this reason, ethers should n ever be distilled to dryness. ) (b ) Peroxide formation can be prevented by excluding oxygen. Ethers can be checked for the presence of peroxides, and peroxides can be destroyed safely by treatment with reducing a gents . (a ) Beginning with (R)-butan-2-o l and producing the (R) sulfide requires two inversions of configuration. H Br HO H 1 4-35 1 4-34 � R � 5 (b) Synthesis of the (5) isomer directly requires only one inversion . HO H An a lternative approach would be to make the tosylate, displace with chloride or bromide (SN2 with inversion ) , then do a second inversion with Na SCH3. Ts O H R � R T sCI pyridine � ./ .-. 1 4-36 (a ) � ......,., molecular ion mlz 1 02 mlz 73 ))� } " C H2 3 10 ...
View Full Document

This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

Ask a homework question - tutors are online