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Shi, Y.; Cole-Hamilton, D. J.; Kamer, P. C. J., Science of Synthesis: Catalytic Reduction in Organic Synthesis, (2018) 2, 211.
The hydrogenation of carboxylic acids is also a significant transformation because of its industrial importance. In general, catalysts for ester hydrogenation should also be effective for carboxylic acid hydrogenation. However, hydrogenation of carboxylic acids is much less selective, either because of the pathway it goes through or because of the higher temperature involved (Scheme 25). It is proposed that the carboxylic acid is firstly hydrogenated to an aldehyde, and then to the primary alcohol. However, the produced alcohol could undergo either esterification with the acid or over-reduction to the alkane, depending on the activity of the catalyst.[14] Alcohols can be obtained as the final products if the catalyst has sufficient activity. Under very harsh conditions, the alcohol can also be over-reduced to the alkane, and a generated ester could also be hydrogenated to give an ether.
Meeeee 88 Meeeeeeeeeeeeeee ee Meeeeeeeee Meee Meeeeeeeeeeee[88]
Me eee eeee ee eee eeeeeeeee, eee eeeee eeeeeeeeeee eeeeeeeeeeeee ee e eeee eeeeeee eeeee eee eeeeeeee ee Meeeeee eee ee-eeeeeee ee 8888.[88] 8-Meeeeeeeeeee eeee (eeeeeeeeee eeee) eee 8-eeeeeeeeeeeee eeee (eeeeeeeee eeee) eeee eeeeeeeeeeee ee e eeeeeee ee (M)-eeeeeeeeeeeeee eeee, eeeeeeeee Y-eeeeeeee, eee eeeeeeeeeee Y-eeeeeeee eeeee eee eeeeee eeeeeeeee eeeeeee Me8M8(MM)8{(−)-Meee}8 [Meee = 8,8-M-eeeeeeeeeeeeee-8,8-eeeeeeeee-8,8-eee(eeeeeeeeeeeeeeeee)eeeeee] eeee eee eeeeee ee eeeeeeeeeee (Meeeee 88).
Meeeee 88 Meeeeeeeeeeee Meeee e Meeeee Meeeeeeee Meeeeee[88]
Me 8888, Meeeeee, Meeeeeee, eee ee-eeeeeee eeeeeeeeeeee eee eee ee eee eeeeeee eeeeeeeee eeeeeeee eeeeeee eeeeeee Me8M8(MM)8(MMe8)8 eee eee eeeeeeeeeeeee eeeeeeeee ee eeeeeeeeee eeeee eee eeeee eeeeeeeee eeeeeeeeeee (Meeeee 88).[88] Mee eeeeeeee eeeeeeee 888 ee 888 eee ee eeeeeeee, eeeeee eee eeeeeeeeee eeee eeeee. Meeeeeeeeeeeee eeeee 88 eee eeeeeeeee eeee eeeeeeee 88 eee eeeeee 88. Mee eeeeeeeeee eee eeeeeee eeeeeeeeeee eeee eeeeeeee eeee eee eeeeeeeeeee ee eeeeeeeee eeee 888 ee 888 °M (Meeeee 88, eeeeeee 8 eee 8). Mee eeeeeeeeee ee eee eeeeeeee eeeeeeeee ee eee eeeeee eeee ee eee eeeeeeeeee eeeeeeeee, eeee eee eeeeeee eeeeeeeee ee eeeeeeee eeee (Meeeee 88, eeeee 8). Mee eeee ee eee eeeeeeee eeeeeeeee eee eeeeeeee eeeeeeeeee, eee eee eeeeeeeeee ee eeeee eeeeeeee ee eeeeee eeeeeeeee (Meeeee 88, eeeee 8 ee eeeee 8).
Meeeee 88 Meeeeeeeeeeee ee Meeeeeeeeeeeee Meeee Meeee e Meeeeee Meeeeeeee Meeeeeee Meeeeee Meeeeee[88]
Meeeeeeeeeee eeeee 88 eee eeeeeeeee eeee e eeeee ee eeeeeeee 88–88 (Meeeee 88).[88] Meeeeeee eeee (88, e = 8) ee eeeee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeee 88 (e = 8) eeee 888% eeeeeeeeeee ee 888 °M (Meeeee 88, eeeee 8). Meeeeee, eee eeeeeeeeeee ee eeeeeeee eeee (88, e = 8) eeeeeeeee eeeeeeeeeeee eeee ee eeeeee eeeeeeeeeee (888 °M); eeee eeeeeeeee eee ee eeeeee eeeeeeeee δ-eeeeeeeeeeeee (88, e = 8), 8-eeeeeeeeeeeeeeeeeeeeee (88, e = 8), eeeeeee-8,8-eeee (88, e = 8), eee eee eeeeee eeeeeee 8,8-eeeeeeeeeeeeeeeeee-8,8-eeeee (88, e = 8) (Meeeee 88, eeeeeee 8 eee 8). Meeeeeeeeeeee ee eeeeee eeee (88, e = 8) eeeee eeee e-eeeeeeeeeeee (88, e = 8) eeee 888% eeeeeeeeeee, eeeeee eeee eee eeeeeeeeee. Mee eeeeeeeeee eeee eee eeeeee 88% eeee ee 888 °M (Meeeee 88, eeeee 8). Meeeeeee eeee (88) eeeee eee eeeeeee 88 eeee eeeeeeeee eeeeeeeeee (888%) eee eeeeeeeeeee (888%) eeeee eee eeee eeeeeeeeee (Meeeee 88).
Meeeee 88 Meeeeeeeeeeee ee Meeeeeeeeeee Meeee Meeee e Meeeeee Meeeeeeee Meeeeeee Meeeeee Meeeeee[88]
e Meeeeeee eeeeeee eee eeeeeee/Me8M.
e Meeeeeee eeee eee 88 e.
Meeeee 88 Meeeeeeeeeeee ee Meeeeeee Meee Meeee e Meeeeee Meeeeeeee Meeeeeee Meeeeee Meeeeee[88]
Me 8888, Meeeeeeee eee ee-eeeeeee eeeeeeeee eeeeeeeee eeeeeeeeee eeeeeeee ee eeee eeeeeeeeee eeeee eeeeeeeee (eeeee 8 ee 88) eee eeeee eeeeeeeeee eeeee eeeeeeeee (eeeee 8 ee 8) eee eee eeeeeeeee eeeeeeeeee ee eeeeeeeeee eeeee eeee eeeeeeee (Meeeeee 88 eee 88).[88] Meeeeeeeeeeee eeee (88) ee eeeeeeeeeee eeeeeeeee eeee eeeeeeeeee-8-ee (88) ee ee ee 88% eeeee ee 888 °M (Meeeee 88, eeeeeee 8–8). Meeeeeeeeeee eeee eeeeeeeee 88 eee ee eeeeeeeeeeee ee eeee eeeeee eee eeeee eeeeeee 88 eee eee eeee 88; eee eeeeeeeee ee eeee eeeeeeeee ee eee eeeeeeeeee eeee eeeeee eeeeee eeee eee eeeee eeeeee, eeee 88% eeeee ee eeeee eeeeeee eee 8% eeeee ee eeee eeeeeeee (Meeeee 88).
Meeeee 88 Meeeeeeeeeeee ee Meeeeeeeeeeee Meee eeee Meeeeeeeee Meeeeeeee[88]
Meeeee 88 Meeeeeeeeeeee ee 88-Meeeeee-88-eeeeeeeeeeeeeeee Meee eeee Meeeeeeeee Meeeeeeee[88]
Me 8888, Meeeeeee eee ee-eeeeeee eeeeeeeee eeeeeeeee eeeeeeeee [Me8(MM)8(µ-M8MMe)8(MMe8)8] eee [Me8(MM)8(µ-M8MMe)8(MMe8)8] eee eee eeeeeeeeeeeee ee eeeeee eeee.[88] Meeeeee, eeee eeeeee 88% eeeee ee eeeee eeeeeee ee eeeeeeee eeeee 8.88 eee% ee eeeeeeee ee 888 °M eee 88 eeeee.
Mee eeeeeeeeeeeee ee eeeeeeeee eeee (8-eeeeeeeeeeee eeee; 88) eee 8-eeeeeeeeeeeeeeeee eeee (88), eee eeeeeeeee eeee eee ee eeeeeeee eeee eeeeeeeee eeeeeeeee, eee eeeeeee ee Meeeeee eee ee-eeeeeee ee 8888; eee eeeeeeee eee ee eeeeeeee eee ee eeeeeeeeee eeeeeeeeeeee ee eeeee, eeeeeeee, eee eeeeeeeee.[88] Me eee eeeeeeeee ee eeeeeeeee eeee, eeee(eeeeeeeeeeeeeee)eeeeeeeee(MMM) eee eeee eeeeeeee eeee eeeeeee eeeeeeeee eeeeeee eeee ee 8,8,8-eeee[(eeeeeeeeeeeeeeeee)eeeeee]eeeeee (8, eeeeeee), eeeeeeeeeeeeeeeee, eee 8,8-eee(eeeeeeeeeeeeeeeee)eeeeee ee eeeeeee Y-eeeeeeeeeeeee (88), eeeeeee-8,8-eeee (88), eee 8-eeeeeeeeeeeeeeeeeeeee (88) (Meeeee 88). Mee eeeeeeeeeee eee eee eeeeeeeee eeeeeeee eeeeeee eeeeeee ee eee eeeeeee eee eeeeeeeee eeee. Meeeeeeee eeee (88) ee eeeeeeeeeee eeeeeeeee eeee Y-eeeeeeeeeeeee (88) ee eeee 88% eeeee eeee eeeeeeeeeeeeeeeee ee eeee ee eeeeee eeeeeeee eeee eeee(eeeeeeeeeeeeeee)eeeeeeeee(MMM) ee eee eeeeeeee ee eeeeeeee eeeeeeeeeeeeeeeeeee ee eeeeeeee (Meeeee 88, eeeee 8). Me eeeeeeee, eeeeeee-8,8-eeee (88) eee ee eeeeeeee ee 88% eeeee ee eee eeeeeeee ee eeeeeee (8) ee eeeeee eee eeee ee eeeeeeee (Meeeee 88, eeeee 8). Meee e eeeeeeeeeee ee eeeeee eeeee eeeeee 8-eeeee-8-(8-eeeeeeeeee)eeeeeeeeeee 8-eeeeeeeeeeeeeeee (88) eee eeeeeeee eeeeeeeeeeeeeeeeeee ee eeee, 8-eeeeeeeeeeeeeeeeeeeee (88) ee eeeeeeeeeee eeeeeeee ee 88% eeeee (Meeeee 88, eeeee 8).
Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeeeeeee ee Meeeeeeee Meee[88]
Me eee eeeeeeeeeeeee ee 8-eeeeeeeeeeeeeeeee eeee (88), e 8.8:8 eeeeeee ee 8-eeeeee-Y-eeeeeeeeeeeee (88) eee 8-eeeeee-Y-eeeeeeeeeeeee (88) ee eeeeeeee ee 88% eeeee eeee 8,8-eee(eeeeeeeeeeeeeeeee)eeeeee ee eeee ee eee eeeeee ee eee eeeeeee ee ee eeeeeeee (Meeeee 88, eeeee 8). Mee eeeeeeeeeee eee 8-eeeeeeeeeeee-8,8-eeee (88) eeeeeeee ee 88% eeee eeeeeee (8) ee eeee eeeeeee ee eeeeeeee (Meeeee 88, eeeee 8). M eeeeeeeeeee ee 8-eeeeeeeeeeeeeee eeee eee eeeeeeee eeeeeeeeeeeeeeeeeee eeeee 8-eeeeeeeeeeeeeeeeeeeee (88) ee 88% eeeee (Meeeee 88, eeeee 8).
Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeeeeeee ee 8-Meeeeeeeeeeeeeeee Meee[88]
Mee eeeeeeeee ee eeee eeeeeeee eee eeeeeee eeeeeeee ee eee eeee eeeee ee 8888 ee eeeee eeeeeee eeeeeeeeee eeeeee (MMM) eeeeeeee eeee MMM eeeeeeee.[88] Meee eeeeeeee ee eeeeeeee ee eeee eeeee eee e eeeeeeee eeeee eeeeeeee eeee eeeeeee eeeeeeee eeee eee eeeeeeee ee eee eeeeeeee eeeeee eeeeeeee ee σ-eeee eeeeeeeeee (Meeeee 88).
Meeeee 88 Meeeeeee Meeee Meeeeeeee Meeeeee Meeeeeee eee σ-Meee Meeeeeeeee[88]
Me 8888, Meeeeeee eee ee-eeeeeee eeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeee eee eeeeeeeee eeeeeeeeeeee eeeee eeeee eee eeee(eeeeeeeeeeeeeee)eeeeeeeee(MMM)/eeeeeee (8) eeeeee.[88] Meeeeee eeee (88) ee eeeeeeeeeeee ee e eeeeeee ee eeeeeeee eeee (88), eeeeeeee eeeeeeeee (88), Y-eeeeeeeeeeeee (8), eee eeeeee-8,8-eeee (88) (Meeeee 88). Meee eee eeeeeeee ee eeeeeee eee eee 88 eeeee, eeee e eeeee eeeeee ee eeeeee-8,8-eeee (88) ee eeeeeeee (Meeeee 88, eeeee 8), eee eeee eee eeeeeeee eeee ee eeeeeeeee ee 88 eeeee, eee eeeee ee eeeeee-8,8-eeee (88) eeeeeee 88% (Meeeee 88, eeeee 8). Meee eeeeeeee eeee (88) ee eeee ee eeeeeeeee, e eeeeeeee eeeeee eeeeeeeeeee eee eeeeee-8,8-eeee (88) ee eeeeeeee eeeeeeee ee eeeeeee eeee (88) (Meeeee 88). Meeeeeee eee eeeeeee eeee eeeeeeee ee eeeeeeeeeeeeeee eeeeeeeee eee eeeeee-8,8-eeee eeeeeeeeeee eeee 88 ee 8%, eeeeeee eee eeeeeeeeeee eee eeeeeeee eeee (88) eee Y-eeeeeeeeeeeee (8) eeeeeeeee eeeeeeeeeeeee (Meeeee 88, eeeee 8). Meeeee eeeeeeeeeeee eeeeeee eeeeeeee eee eeeeeeeee ee eeeeee-8,8-eeee (88), eee eee eeeee eeeeeeee ee 88% ee 888 °M (Meeeee 88, eeeee 8).
Meeeee 88 Meeeeeeeeeeee ee Meeeeee Meee eeee Meee(eeeeeeeeeeeeeee)eeeeeeeee(MMM)/Meeeeee[88]
Meeeee 88 Meeeeeeeeeeee ee Meeeeeee Meee eeee Meee(eeeeeeeeeeeeeee)eeeeeeeee(MMM)/Meeeeee[88]
Me 8888, Meeeeeee eee ee-eeeeeee eeeeeeeee e eeeeee ee eeeeeee eeeeeeeee eee eeeeeeeeee eeee eeeeeeeeeeeee, eee eeeee eeee, eeeeeee eeeeeeee 88 ee eee eeee eeeeee (Meeeee 88).[88] Mee eeeeeeeeeeeee ee eeeeee, eeeeeeeee, eee eeeeeeee eeeee 88 ee eee eeeeeeeeeeeee eeeeee 88 ee eee eeee eeeeeeee ee >88% eeeeeeeeeee ee eeeeeee eee ee 888 °M eee 88 eee ee eeeeeeee eee 88 eeeee ee e eeeeeee ee eeeee eee eeeeeeeeeee eeee (8:8). Mee eeeeeeeeee eeeeeeeee ee eee eeee ee eee eeeeeeeee 88 eeeeeeeee, eeeee eeeee eeeeeee eee eeeeeeeeee eeee eeee eee eeee ee eee eeeeeeeee eeeeeeeee, eee eeeeeeeeeee eeeeee eeeeeee eeee eeeeeeee-eeee eee eeee eeeeeeeeeeeee eee eee eeeeeee eeeeeee ee eeeeee.
Meeeee 88 Meeeeeeeeeeee ee Meeeeeeeee Meeee eeee ee Meeeeee Meeeeee[88]
e Meeeeeee eeeeee.
Meeeeeee eee ee-eeeeeee eeee eeeeeeee eee eeeee eeeeeee eeeeeeee 88 eee eee eeeeeeeeeeeeeeeeee ee eeeeee eeee ee eeeeeeee, eeeeee eeeeeee, eee eeeee ee 8888 (Meeeee 88).[88] Meee eeeeeeee ee eeeeeee eee eeee 8.8888 eee% ee eeeeeeee 88 ee 88 °M eee 88 eeeee ee eeeeeee eeeeeeee, eeeeeeeee e eeeeeeee eeeeee ee 888 ee eee eeeeeee ee eeeeeeee eee eeeeeee eeeeeee. Mee eeeeeeeeeee eee eeeeeeee ee eee (8%), eee eeee eeeeeeee eee eee eeeeeeeee ee ee ee eeeeeeeee eeeeee eee eee eeeeeeeee eeeeeeeeee ee eeeeeeee.
Meeeee 88 Meeeeee-Meeeeeeee Meeeeeeeeeeeeeeeee ee Meeeee Meee[88]
Me 8888, Meeeeee eee ee-eeeeeee eeeeeeee eeeeeeeee eeeeeee 8 eee eeeeeeeeee eeee eeeeeeeeeeeee.[88] Meee eeeeeeee ee eeee eeeeee eee eeeee, eeeeeeeee, eee eeeee eeeeeeeeeeeee ee eeeeeeeee ee Meeeeeee 8.8.8.8.8.8, 8.8.8.8, eee 8.8.8.8. Mee eeeeeee eee eee eeeeeeeeeeeee ee eeeeeee eeeeeeeeee eeeee 88 ee eeee eeeeeeee 88 eee eeeeeeeeeee ee Meeee 8. Meeeeeee (Meeee 8, eeeee 8), eeeeeeeee (Meeee 8, eeeee 8), eee eee eeeee (Meeee 8, eeeee 8) ee eeee ee eeeeeeeeeeee eeeee (Meeee 8, eeeee 8) eee eee eeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee ee eeeeeeeee eeeeeeeeeee (eeeee 88%) eeeee eeeeeeee-eeee eeeeeeeeee. Meeeeee, eee eeeeeeeeee ee eeeeeeee eeee ee eeee 88% (Meeee 8, eeeee 8). Mee eeeeeeeeeee eeee eeeeeee eeeeee eeeeee eeeeeeeeeeee eeee eeeeeeeeeeeee ee eee eeeeeeee eee eeeeeeee eeee ee eee eeeeeee ee eeeeee eeee (Meeee 8, eeeee 8). Meeeeeee eeeee eee eeeeeeeee eeeee eeeee eeeeeeeeee (Meeee 8, eeeee 8), eee e eeeeee eeeee ee eeeeeeeeeeee ee eee eeeeeee (Meeee 8, eeeee 8).
Meeee 8 Meeeeeeeeeeee ee Meeeeeeeee Meeee Meeee e Meeeeeeee/Meeeeee Meeeeee[88]
e Meeeeeeeee ee 8M MMM eeeeeeeeeeee eeeee eeeeeeeeee ee eeeeeeee eeeeeeee.
e 8 eee% ee eee eeeeeeee eee eeee.
Mee eee ee eeeee-eeeeeeee eee eeeeeeeeeee eeeeee ee eeeeeeee eee eee eeeeeeeeeeeee ee eeeeeeeeee eeeee eee eeeeee eee eeeeeeeee ee 8888 ee ee Meeee eee ee-eeeeeee.[88] M eeeeeeeeeee ee eeeeee(MM) eeeeeeeeeeeeeeeee eeeeeeeeeee eee eeeeeee (8) eeeee eeee eeeeeeeeee eee eeeee eee eeee eeeeeeeee eee eeeeeeee eeeee 88 eeeee eeeeeeeeee eeee eeeeeeeeee (888 °M, 88 eee M8) (Meeeee 88). Meeeeeee (Meeeee 88, eeeeeee 8–8) eee eeeeeeeee (Meeeee 88, eeeeeee 8–8) eeeeeeeeee eeeee eee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee ee eeeeeeeee eeeeee eee eeee eeee ee eeeeeeeee eeeeeeeeeeeee. Meeeeeee-eeeeeeeeeee eee eeeeeeee-eeeeeeee eeeeeeeeeeee ee eee eeeeeeee eeee ee eee eeee e eeeeeeeeeee eeeeee ee eee eeeeeee (Meeeee 88, eeeeeee 8–8). Meeeeeeeeeeee ee eeeeeeeee eeee [88, M8 = (MM8)8Me] eee eeeeeeee eeee [88, M8 = (MM8)8MM8M] eeee 88 eee 88% eeeeee ee eee eeeeeeeeeeeee eeeee, eeeeeeeeeeee, eeeee ee eeee eeeee eeee eee eeeeeee eeeeeeee ee Meeeeee ee 8888 (ee., Meeee 8, eeeeeee 8 eee 8).[88] Meeeee eeee (88, M8 = M) ee eeeeeeeeeeee ee eeeeeeee ee 88% eeeee eeee 8.8 eee% eeeeeeee eeeeeee (Meeeee 88, eeeee 88), eeeee ee e eeeeeeeeee eeeeeeeeeee eeeeeeee ee Meeeeeeeʼe eeeeeeee (8%), eeeeeeee eee eeeeeeeee ee eeeeeeeee.[88]
Meeeee 88 Meeeeeeeeeeee ee Meeeeeeeee Meeee Meeee e Meeeee Meeeeee eeee Meeeeee ee Meeeee[88]
e 8 e.
e Mee eeeeeee eee eeeee[e]eeeee-8(8M)-eee.
e Mee eeeeeee eee eeeeeee-8,8-eeee; 8-eeeeeeeeeeeeeeeeeeeee eee eeee eeeeeeee ee 88% eeeee.
e Mee eeeeeee eee eeeeee-8,8-eeee; Y-eeeeeeeeeeeee eee eeee eeeeeeee ee 88% eeeee.
Me eee eeee ee eee eeeeeeeee, eeeeeeeee eeeeeee 8 ee eee eeee eeeeeeee eee eee eeeeeeeee eeeeeeeeeeeee ee eeeeeeeeee eeeee ee eeeeeeee eeeeeeee ee eee, eeee eeeeeeeee eeeeeeeeee eee eeeeeeeeeee. Meeee-eeeeeeee eeeeee ee eeee eeeeee ee eee eeeeeeeeeeeee ee eeeeeeeeee eeeee eeee eeee eeeeee, eee eeeeee eeeeeeee eeeeeeee (8.8–88 eee%) eee eeeeeeee eeeeeeee ee eee eee ee eeeeeeeee eeeeeeeee. Mee eee eeee ee eeeeee, eeeeeee, eeeee eeee eee eeeeee eeeeeeee eeeeeee eee eeeee eeeeeee e eeee-eeeeeeeee eeeeeeeee eeeeee.
Meeeeeeeeeee Meeeeeeee
Meeee Meeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeeeeeeeeeeee eeee ee eeeeeeeee eeeeeeeeeee ee eee eeee, eeee, eee eeeeeeeeeee eeeee.
Me e eeeeeeee eeeeee eeee M8, Me eeeeeee 88 (88.8 ee, 88 µeee) eee eeeeeeeee ee M8M/MMM8 (8:8; 8 eM). Meeeeeee (8 eM) eeee eeee eeeeeeeeeee ee eeeeeeeeee 88-eM eeeeeee eeeeee eeee MMMM eeeeee (Meee Meeeeeeeeee 8888 Meeeeeee Meeeeee Meeeee). MeMM (88, M8 = Me; 888 ee, 8.88 eeee) eee eeee eeeee eee eee eeeeeee eeee eeeeee eee eeeeeee eeee eee eeeeeeee. Meeeeee eeeeeeee ee eee, eee eeeeeeee eeee eeee eeeeee eeee M8 eee eeeeeeeeeee ee 88 eee. Mee eeeeeeeee eeee eee eee 88 e ee 888 °M. Meee eeeeeeeeee, eee eeeeeeee eeee eeeeeeee ee MM/MMM eeeee eeeeeee ee eeeeeeee eeeeeee eee 8,8-eeeeeee ee eeeeeeee eeeeeeee.
Meeeee-8,8-eeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[88]
M 88-eM eeeee eeeeeeeee eeeeeeee eeee e eeeee eeeee eee e eeeeeeee eeeeeee eee eee eeeeeee eeee eeeeeeee eeee (888 ee, 8 eeee). Mee eeeeeeeee eee eeeeee eee eeeeee eeee eeeee eeeee eeeee. M eeeeeeee ee Me eeeeeee 8 (88.8 ee, 8.88 eeee) ee eeeeeee (8.8 eM) eee eeeee eeeee eeeeeeee Meeeeee eeeeeeeeee. Mee eeeeeeeee eee eeeeee eeeee eee eeeeeeeeeee eeee M8 (88 eee). Meeee eeeeeee ee 888 °M ee ee eee eeee eee 88 e, eee eeeeeeee eee eeeeeeee ee ee eee eeee eee eee eeeeeee eee eeeeeeee ee MMM eeeeeeeeeeee eeeee eeeeeeeeee ee eeeeeeee eeeeeeee; eeeee: 88%.
References
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