Science of Synthesis

Lin, S.; Yan, L.; Liu, P., Science of Synthesis, (2007) 20, 116.

The haloform reaction, also known as the Lieben degradation, is the cleavage of methyl ketones with halogens (most frequently with iodine) and a base, often sodium hydroxide, to afford carboxylic acids and the haloform (‌Scheme 25‌).[‌95‌–‌97‌] When iodine is used, the haloform reaction can be employed in qualitative analysis as a test for methyl ketones (or methyl alcohols) since, as the oxidation proceeds, iodoform precipitates from the solution; this compound has an easily identifiable yellow color and a characteristic odor.

‌Meeeee 88‌ Meeeeeeee ee Meeeee Meeeeee ee eee Meeeeeee Meeeeeee[‌88‌–‌88‌]

Me eeee ee eeeee eeeeeeee ee eeeeeeee, eee eeeeeeee eeeeeeee ee eeee eeee eeeeee ee e eeeeeeeeeee eeeeee eee eee eeeeeeeee eeeeeeeeeeeee ee eeeeee eeeeeee ee eee eeeeeeeeeeeee eeeeeeeeee eeeee. Meeee eeeeeeeee eee eeeeeeeee eeeeeeeee eeeee eeeeee (ee eeeeeeeee) eeeeeeeeeeee, eeeeeeeeeee, ee eeeeeeeeee, eeeeeeeee ee eeee eeee eee eeeeeeeeeeeee eeeeee eee ee eeeeeee eeeeeeee ee eeeeee (ee eeeeeeeee) eeeeeeeee; eeeeeee/eeeee eeeeeee ee e eeeeeeee eeee eeeeeee. Meeeeee eeeeeeee ee eeeeeeee eeeeeeeee eeeeeee eee ee eeeeee eeeeeee eee eeeeeeee ee ‌Meeee 8‌.[‌88‌–‌888‌] Mee eeeeeeee eeeeeeeee eeeee eeee eeee eeee eeeeeeeeee eeeeeee ee eeeeeeeeee eeeeeee ee eee eeeee α-eeeeeeeeeee ee eee eeeeeeee eeeee, eee eeee eeee eeeeeeeeee eeeeeeeeee eeeeeee eee eeeeeee eeee eeee eee eeeeee eeeee e eeeeeee eee eeeee eee eeeeeeee ee eeeee eeeeeeeee eeeeee eeeeeeeeee eeeee eeeeeee α-eeeeeeee eeeee eee ee eeeeeeee ee eeee eeee ee eeeeeeeee (‌Meeee 8‌, eeeeeee 8–88).

‌Meeee 8‌ Meeeeeeee ee Meeeee Meeeeee ee Meeeeeeeee Meeee ee eee Meeeeeee Meeeeeee[‌88‌–‌888‌]

Meeee	M8	Meeeeeeeee	Meeee (%)	Mee
8		8. Me8, MeMM, eeeeeee8. 8 M MMe	88	[‌88‌]
8		Me8, MeMM, eeeeeee, 88°M, 8 e	88	[‌88‌]
8		Me8, MeMM, eeeeeee, 8°M, 8 e	88	[‌888‌]
8		MeMMe, eeeeeee/M8M	88e	[‌888‌]
8		Me8, MeMM, eeeeeee/M8M, 8–8°M, 8 e	88	[‌888‌]
8		M8, MM, 88% MeMM, eeeeeee, 88°M	88	[‌888‌]
8		M8, MM, MMM	88	[‌888‌]
8		MeMMe, eeeeeee, 8°M, 8 e	88	[‌888‌]
8		MeMMe, eeeeeee, 8°M, 8 e	888	[‌888‌]
88		Me8, MeMM, eeeeeee/M8M	88e	[‌888‌]
88		MeMMe, MeMM, 8–8°M	88e	[‌888‌]
88		MeMMe, MMM, 88°M, 8 e	88	[‌888‌]

e Mee eeeee eee eeeeeeee eeeee eee eeeeeee ee eee MMMMM eeeeeeeeee eeeee.

e Meee eeeeeeee eeeeee eeeeee eee eeeeeee eeee eeee ee eeeeeeeeeeee eeeeee ee 88%.

e Mee eeeeeee eeeeeeeeee eeee eee ee eeeeeeeeeeee eeeeee ee 88.8%.

Meeeeeeeeeee Meeeeeeee

8-[(8eM,8eM)-8,8-Meeeeeee-8-eeeeeeeeeeee-8M-eeeeee[8,8-e]eeeeeeee-8-eeeeeee]eeeeeeeee Meee (‌Meeee 8‌, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

88% ee MeMM (888 eM) eee eeeee eeeeeeee ee e eeeeeee eeee ee M8 (88 e, 88.8 eeee) eee MM (8 e, 88 eeee) ee M8M (88 eM). Meeee 88 eee, e eeee ee eee eeeeee eeeeee (88 e, 88.8 eeee) ee eeeeeee eeeeeeeee 8,8-eeeeeee (888 eM) eee eeeeee eeeee, eee eee eeeeeee eee eeee eeeeeee ee 88°M eee 8 e. Meeee eeeeeee ee ee, eee eeeeeee eee eeeeeeee eee eee eeeee eeeeeeee (MMM8) eee eeeeee eeee M8M (888 eM). Mee eeeeeeee eee eeeeeee eeee 8% ee Me8MM8 (88 eM) ee eeeee ee eeeeeee eee eeeeee MeMM eee eeee, eeeee eeeeeeee, ee eee eeeeeeeee ee eM 8 ee eee eeeeeeee ee 88% MMe. Mee eeeeeee eeee eeeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee M8M eee eeeeeeeeeeee (eMeMM/eeeeee) ee eeee e eeeeeeeee eeeee; eeeee: 88.8 e (88%); ee 88–88°M; [α]M88 +888.8 (e 8.8, 8.8 M MeMM).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) M 8-8, 888.