{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Solutions_Manual_for_Organic_Chemistry_6th_Ed 423

Solutions_Manual_for_Organic_Chemistry_6th_Ed 423 - 18-43...

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

View Full Document Right Arrow Icon
18-43 C6H J 002 indicates two elements of unsaturation. The IR absorption at 1708 em· 1 suggests a ketone, or possibly two ketones since there are two oxygens and two elements of unsaturation. The NMR singlets in the ratio of 2 : 3 indicate a highly symmetric molecule. The singlet at (5 2.15 is probably methyl next to carbonyl, and the singlet at (5 2.67 integrating to two is likely to be CH2 on the other side of the carbonyl. > o o II II H3C -C -CH2 -CH2 -C -CH3 Since the molecular formula is double this fragment, the molecule must be twice the fragment. Two questions arise. Why is the integration 2 : 3 and not 4 : 6? Integration provides a ratio, not absolute numbers, of hydrogens. Why don't the two methylenes show splitting? Adjacent, identical hydrogens, with identical chemical shifts, do not split each other; the signals
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

Ask a homework question - tutors are online