424 TRANSACTIONS OF SECTION B. > 
would be the gain to an Honours graduate working for the M.Sc. degree, if, 
instead of being associated with the same teacher during the whole of his 
academic career, he could migrate from the place which had trained him to spend 
part, or the whole, of his time in the laboratory of an Armstrong. a Donnan, a 
Perkin, or a Ramsay, during that most critical period when he is sorting out his 
own ideas and learning how to use his fingers and his wits. But whether 
enforcement of the longer training for the Honours degree be possible; whether 
a research degree as a step to the Doctorate be desirable or practicable, there 
can be no doubt that the urgent need of the present time is the provision of 
scholarships and exhibitions, sufficient in value to secure at least a bare liveli- 
hood, for post-graduate work. He who is able to convert Education Committees 
and private donors to the view that a far better return for the money could 
be assured if part of the large expenditure on scholarships for matriculated 
or non-matriculated students were diverted to post-graduate purposes, will have 
done a service to science and the State the value of which, in my opinion, 
cannot be overestimated. 
The following Papers and Reports were then read :— 
1. The Progressive Bromination of Toluene. 
By Juuius B. Coney, F.R.S., and P. K. Durt, 
A. K. Miller 1 studied the action of bromine on ortho- and para-bromotoluene 
separately and identified the dibromotoluenes formed in each case by oxidising 
the products to the corresponding benzoic acids and fractionally crystallising 
the barium salts. His results may be summarised as follows : Ortho-bromotoluene 
gave the 2 :5 dibromo- compound as the principal product together with a 
smaller quantity of the 2:4 derivative; para-bromotoluene gave, as the main 
product, 3: 4 derivative and a smaller quantity of the 2: 4 compound. 
In comparing these results with those of chlorination of ortho- and para- 
chlorotoluenes* considerable discrepancies appear. In the case of chlorination 
of ortho-chlorotoluene the main products were the 2 : 4 and 2 : 3, and a similar 
quantity of 2:6 derivative, whilst the presence of 2:5 compound seemed 
probable but not certain. In the case of the para- compound, the 2:4 is the 
main product and not 3 : 4, as found by Miller in the case of bromination. 
Considering this difference in the orienting effect of the two halogens we 
thought it desirable to repeat Miller’s work and extend it along the same lines 
as were followed in the case of chlorination. 
Incidentally, we examined the mixed monobromo-toluenes—the first product 
of the action of bromine on toluene—to detect any trace of the nieta- compound 
if formed. We also carried our investigation as far as the tribromo- stage. 
In the following table the results of bromination and chlorination are given 
side by side, the principal product being placed first in each case and a trace 
indicated by brackets :— 
| => | Bromination Products | Chlorination Products | 
| Toluene. | Ortho-, para- (meta). | Ortho-, para-. 
Ortho- compound. 2353224. een Seis PS. 7.6 (i 
| Monohalogen | | (2: 5). 
| Compounds } Para- 5 2:4; 3:4. 2:4; 3:4. 
Meta- 43 Ay ais orayo ke (ey a) Died, sebieas 
| Weis} Die OMe oles 2D 4s 
2: 4. 22435; (2:4: 6) 2:4:'5; 2:33:43 
(2:4: 6). 
Dihalogen | 2 easy Plt Wars opel Gigs a3) 223 165° 2 oe a 
Compounds (2:3: 6). | 
2:6 Ze: Os | 2:3: 6. | 
3:4. PARC BENS SHN Gi: Sys) Kiet | Re Ba 
3:5. | PFS a) 2:3:5. | 
' Trans. Chem. Soc. 1892, 61, 1023 
2 Cohen and Dakin, 7'rans, Chem, Soc. 1901, 79, 1111. 
