Question

Fri Oct 25 17:13:02 2019 (GMT-04:00) 2664.85 % Transmittance 755.12 1346.49 1297.16256.13 1237.08173.61439.48 889.8844.4988.93 556.21 3345.36 2927.52 2854.91 1451.55363.76 1067.17 1025.44 969.35 405.86 -20 4000 3500 3000 1500 1000 500 2500 2000 Wavenumbers (cm-1) Fri Oct 25 17:13:36 2019 (GMT-04:00) FIND PEAKS: Spectrum: Fri Oct 25 17:13:02 2019 (GMT-04:00) Region: 4000.00 400.00 Absolute threshold:21.686 Sensitivity: 50 Peak list: Position: 405.86 Intensity: -1.399 Position: 556.21 Intensity: 4.429 Position: 755.12 Intensity: 15.782 Position: 788.93 Intensity: 17.828 Position: 844.49 Intensity: 13.383 Position: 889.86 Intensity: 8.106 Position: 969.35 Intensity: 1.003 Position: 1025.44 Intensity: 4.253

Identify the SPECIFIC compound.

Boiling Point: 160 - 175 ° C (Fluctuates)

Water Insoluble
NaOH Insoluble
HCl insoluble (Nitro is absent)
H2SO4 Insoluble
Group X - Inert Compounds
(a) Alkyl and Aryl Compounds
(b) Aromatic Hydrocarbons
(c) Saturated Hydrocarbons
(d) Diaryl ethers

Failed Friedel - Crafts test (no color)

Answer 1

Unknown compound Soluble Water Insoluble 5% NaOH Soluble Insoluble 5% HCI Insoluble Soluble Conc. H2SO4 Soluble Insoluble No color change Saturated hydrocarbons, haloalkanes, aryl halides, other deactivated aromatic compounds, diaryl ethers

• As the compound gives negative Friedel-Crafts test, it can not be an aromatic compound.
• the boiling point shows that it should be alkyl iodide, as among halogens iodo- compounds have higher boiling point than the corresponding bromo, chloro or fluoro derivatives due to the higher molecular weight of iodine.
• two methyl groups are present in the molecule corresponding to 2927 cm^-1 and 2854 cm^-1

The compound could be 2-Iodo-2,3-dimethylbutane.

For confirmation one can perform 1H NMR, 13C NMR, etc