Organic Solvent Properties

Below is the list of solvents along with density, melting point, boiling point, Formula weight.  I have also inlcuded CAS no so that it will be helpful to you during your work.  Please bring to my notice if there is any mistake in this list.:)

Solvent	CAS No	FW	MP	BP	Density
Acetone	67-64-1	58.08	-94	56	0.791
Acetonitrile	75-05-8	41.05	-48	82	0.786
Benzene	71-43-2	78.11	5	80	0.874
Benzonitrile	100-47-0	103.12	-13	188	1.010
1-Butanol	71-36-3	74.12	-90	117.7	0.810
2-Butanone	78-93-3	72.11	-87	80	0.805
Butyl acetate	123-86-4	116.16	-78	124-126	0.882
tert-Butyl methyl ether	1634-04-4	88.15	--	53-56	0.74
Carbon disulfide	75-15-0	76.14	-112	46	1.266
Carbon tetrachloride	56-23-5	153.82	-23	77	1.594
Chlorobenzene	108-90-7	112.56	-45	132	1.107
1-Chlorobutane	109-69-3	92.57	-123	77-78	0.886
Chloroform	67-66-3	119.38	-63	60.5-61.5	1.492
Cyclohexane	110-82-7	84.16	6.5	80.7-81	0.779
Cyclopentane	287-92-3	70.14	-94	50	0.751
1,2-Dichlorobenzene	95-50-1	147	-18 to -15	179-180	1.306
1,2-Dichloroethane	107-06-2	98.96	-35	83	1.256
Dichloromethane	75-09-2	84.93	-97	39.8-40	1.325
N,N-Dimethylacetamide	127-19-5	87.12	-20	164.5-166	0.937
N,N-Dimethylformamide	68-12-2	73.10	-61	153	0.944
1,4-Dioxane	123-91-1	88.11	11.8	100-102	1.034
Ether	60-29-7	74.12	-116	34.6	0.708
2-Ethoxyethyl ether	112-36-7	162.23	--	180-190	0.909
Ethyl acetate	141-78-6	88.11	-84	76.5-77.5	0.902
Ethyl alcohol	64-17-5	46.07	-130	78	0.785
Ethylene glycol dimethyl ether	110-71-4	90.12	-58	85	0.867
Heptane	142-82-5	100.21	-91	98	0.684
Hexane	110-54-3	86.18	-95	69	0.659
Hexanes	73513-42-5	86.18	--	68-69	0.67
2-Methoxyethanol	109-86-4	76.1	-85	124-125	0.965
2-Methoxyethyl acetate	110-49-6	118.13	-65	145	1.009
Methyl alcohol	67-56-1	32.04	-98	64.6	0.791
2-Methylbutane	78-78-4	72.15	--	30	0.62
4-Methyl-2-pentanone	108-10-1	100.16	-80	117-118	0.8
2-Methyl-1-propanol	78-83-1	74.12	-108	108	0.803
2-Methyl-2-propanol	75-65-0	74.12	25	83	0.786
1-Methyl-2-pyrrolidinone	872-50-4	99.13	-24	81-82 (3)	1.033
Methyl sulfoxide	67-68-5	78.13	18.4	189	1.101
Nitromethane	75-52-5	61.04	-29	100.8-101	1.127
1-Octanol	111-87-5	130.23	-15	196	0.827
Pentane	109-66-0	72.15	-130	35-36	0.626
3-Pentanone	96-22-0	86.13	-40	102	0.853
1-Propanol	71-23-8	60.1	-127	97	0.804
2-Propanol	67-63-0	60.1	-89.5	82.4	0.785
Pyridine	110-86-1	79.1	-42	115	0.978
Tetrachloroethylene	127-18-4	165.83	-22	121	1.623
Tetrahyrdofuran	109-99-9	72.11	-108	67	0.886
Toluene	108-88-3	92.14	-93	111	0.867
1,1,2-Trichlorotrifluoroethane	76-13-1	187.38	-35	47-48	1.575
2,2,4-Trimethylpentane	540-84-1	114.23	-107	98-99	0.692
Water	7732-18-5	18.02	0	100	1
o-Xylene	95-47-6	106.17	-25 to -23	143-145	0.870
p-Xylene	106-42-3	106.17	12-13	138	0.866

Beckmann Rearrangement

The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is an acid-catalyzed rearrangement of an oxime to an amide.  Most commonly used catalysts are Conc.H₂SO₄, HCl, PCl₅,  PCl₃, SOCl₂, ZnO, SiO₂, PPA (Poly phosphoric acid).  Aldoximes are less reactive than ketoximes.  Cyclic oximes yield lactams.

Mechanism of Beckmann rearrangement:

Initially the -OH group of the oxime is protonated. Then 1,2 shift of alkyl group (R¹) onto electron deficient nitrogen and the cleavage of N-O bond occurs simultaneously. 

Always the alkyl group which is 'anti' to the -OH group on nitrogen undergoes 1,2 shift which indicates the concerted nature of the beckmann rearrangement.

Where is it used?

This reagent is useful in ring enlargement of cyclic ketone.  A very good example is the industrial conversion of cyclohexanone to caprolactam, which is used in the manufacture of Nylon-6, involves Beckmann rearrangement

Mechanism of this rearrangement is given below

Also relative migratory aptitude comes in place when there are two different groups as shown below.

Above two isomers for the unsymmetrical oxime are possible.  When these oximes are rearranged mixture of products are formed and the ratio in which they form is same as the isomer ratio in oxime.

Oximes derived from aldehydes are not good for Beckmann rearrangement because of the poor yields for primary amides.  Tosyl chloride forms oxime tosylate which eliminates the stable tosylate anion.  PCl₅ and SOCl₂ induce rearrangement by converting OH to a better leaving group.

Certain ketoximes (oximes of alpha-diketones, alpha-keto acids, alpha-dialkylamino ketones, alpha-hydroxy ketones, beta-keto ethers) can be converted to nitriles by the action of proton or Lewis acids via fragmentation reactions, which are considered side reactions, often these are called as ‘abnormal’ or ‘second order’ Beckmann rearrangements.