Solutions Manual for Organic Chemistry (Wade 6th Ed)

Solutions Manual for Organic Chemistry (Wade 6th Ed) - 1...

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 3-4 1 (c) continued DEPT-90 DEPT-135 CH CH CH CH2 13-42 The multiplicity of the peaks in this off-resonance decoupled spectrum show two different CR's and a C H3. There is only one way to assemble these pieces with three chlorines. Cl I CI I 020-- CH3- CH - CH q CI� 07 5 I 060 d t 1 3-43 There is no evidence for vinyl hydrogens, so the double bond is gone. Integration gives eight hydrogens, so the formula must be C 4HsBr2' and the four carbons must be in a straight chain because the starting material was but-2-ene. From the integration, the four carbons must be present as one C H3, one C H, and two CH2 groups. The methyl is split into a doublet, so it must be adjacent to the C H. The two CH2 groups must follow in succession, with two bromine atoms filling the remaining valences. (The spectrum is complex because the asymmetric carbon atom causes the neighboring protons to be diastereotopic.) H I I d Br H I I I I Br I I H - C- C- C- C-H � 1 3 -44 There is no evidence for vinyl hydrogens, so the compound must be a small, saturated, oxygen­ containing molecule. Starting upfield (toward TMS), the first signal is a 3H triplet; this must be a C H 3 next to a C H2. The C H2 could be the signal at 8 l.5 , but it has six peaks: it must have five neighboring hydrogens, a C H3 on one side and a C H2 on the other side. The third carbon must therefore be a CH2; its signal is a quartet at 0 3 .6 , split by a C H2 and an O H. To be so far downfield, the final C H2 must be bonded to oxygen. The remaining I H signal must be from an O H. The compound must be propan-l-ol. d H H a H c � H b a b c d = = = = 8 4.3 (sextet, I H) 8 3 .6 (triplet, 2H) 8 2 .3 (multiplet, 2H) 0l.7 (doublet, 3H) a b c d = = = = 0 3 .6 (quartet, 2H) 0 3.2 (triplet, I H) 0 1 . 5 (6 peaks, 2 H) 00.9 (triplet, 3 H) 294 ...
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