Solutions_Manual_for_Organic_Chemistry_6th_Ed 190

Solutions_Manual_for_Organic_Chemistry_6th_Ed 190 - 8 -59...

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: 8 -59 continued .. (c ) 1 B r2 � Br � Br Br2 T his structure shows a trans alkene in a to-membered ring, just the rotated view of the structure to the right. � anti a ddition of B r 2 requires t ra ns alkene to gi ve meso product tate around C-2 .. (d) (e) CO � o C l2 (X trans-cyclodecene C! �'" : H �2 Br "" OH B H3 - THF .. ~ OH or ( f) � V-/ or 8 -60 CO � � Hg (OA c h� N aBH _ _ _ _ _ -l.. t, C H30H A ) Unknown X, C SH9Br, h as one element of unsaturation. X r eacts with neither bromi ne nor KMn04, so the unsaturation in X c annot be an alkene; it must be a ri ng. B ) Upon treatment with strong base (t-butoxide), X l oses H and Br to give Y, CSHg, which does react with bromine and KMn0 4 ; it must have an alkene and a ring. Only one isomer is formed. C) Catalytic hydrogenation of Y gives methylcyc lobutane. This is a B IG c l ue because it gi ves the carbon skeleton of the unknown. Y must have a double bond in the methylcyclobutane skeleton, and X m ust have a B r on the methylc yc lobutane skeleton . D ) Ozonolysis of Y gi ves a dialdehyde Z, CSHg0 2' which contains all the original carbons, so the alkene c leaved in the ozonolysis had to be in the ring. Let's consider the possible answers for X a nd see if each fits the information. 1) I KO-t-B u i f this is X .---:f' >U o zonolysis this must be Y; only one product > DOES NOT FIT OZONOLYSIS RESULTS so this c annot be X a nd Y d' ° + O =CH2 more possi bilities on the next page 183 ...
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