1362
Vol. 67
NOTES TABLE I 2,2-DIXETHYL-3,4-OCTADIENAL
8""
O=CH-
-CH=C=CH-CHZ-CH~-CH~
O=CH562 560 1 Singlet sharp
68 67 6 Singlet sharp
304.2 317.7 302.2 317.0 1 1 See inBert of Fig. 1
43-135 45-137
Neat 20% in CC1, 7 Intensities Complex of bands partially resolved
}
C.P.S.
from TNS (internal
standard
TABLE I1 2-BUTYL-2-ETHYL-5-METHYL-3,4-HEXA4DIENAL
/CH3
Bu(n) O=CH-h-CH=C=C,,
I
Et
CHD
I1
Bu( n ) O=CH-
-C
562 558 1 Singlet sharp
CH3
I I
CH=C=
' 6
\
Et 3i-100 37 -100
CHs
295 292
1-1
1
Complex partially resolved
Septet resolved
Neat 102 20% in CC1, 6 Intensities Doublet resolved
102
}
c.p.s. from TMS (internal standard)
the C3 proton of I1 is a well resolved septet (cf. Tables I and 11).
RIUTUAL DIFFUSION I N KOK-IDEAL LIQUID MIXTURES. IV. METHAKOLCARBON TETRACHLORIDE AND DILUTE E T H A N O L CARBON TETRACHLORIDE SOLUTIOSS BY D. K.ANDERSONAND A. L.BABB Department of Chemical Enganeerang, Unzversaty of Vashznyton, Seattle, Washzngton Receaaed August 80,1962
In previous papersl.2 the authors presented diffusion data for associated binary liquid systems. As part of this continuing program, diffusivities have been measFig. 2.-Proton resonance spectrum of 2-butyl-Z-ethyl-5ured for dilute solutions of ethanol in carbon tetrachlornethyl-3,4-hexadienal. Proton signal of C3H: insert (a). ride and the methanol-carbon tetrachloride system coupling between the spins of the C6-methyleneand the over the entire concentration range. C6-proton (J6,6= 6.5 c.P.s.) is the same as that of The mutual diffusion coefficients were measured comparable protons in other 01efins.~ The coupling using a Mach-Zehnder diffusiometer described fully between the spins of the C6-methylene and the C3- elsewhere. Temperatures were controlled a t 25.0 f proton (J3,6= 3.3 c.P.s.) compares well with a com0.05'. The reagent grade solvents were obtained from parable parameter which was determined from the blallinckrodt Chemical Works and were used without n.m.r. spectrum of 3-methyl-l,2-butadiene by Snyder further purification. and R ~ b e r t s . ~ Similarly, the spin-coupling between The diffusivities were obtained by measuring the the protons of the terminal methyl groups and the interdiffusion of two solutions of very nearly equal conallenic proton in 2-butyl-2-ethyl-3-methyl-3,4-hexa- centration. The measured value was taken to be that dienaI (1I)lwas found to have about the same coupling of a solution with a concentration equal to the average of constant ( J = 3.0 c.P.s.). the two. The results are given in Tables I and 11. KOevidence of any spin-coupling between the allenic Although data were previously available4 for the protons and the protons of the substituents on CZ of ethanol-carbon tetrachloride system, a seriep, of detereither compound could be detected. The signal for (1) D. K. Anderson and A. L. B a b b , J . Phys. Chem., 65, 1281 (1961). the C2-methyl groups of I was sharp, and the signal of (2) D. I
