Espinosa, CHM212B

Name: Alba Roselia Espinosa Peguero

Date: 22, February, 2024

Qualitative Analysis Report

Unknown Name and Structure:

1-chlorobutane

Measured Boiling Point: N78 Measured Melting Point: N/A n20D 1.4022
Color/morphology: colorless/white liquid Odor (if any detected): N/A Solubility
Classification (if determined): not determined

Chemical classification tests (Report all. DNPH, Chromic, and Br2 are required):
Test Name Detailed Visual Description of Results Conclusions
(colors observed, other details)
DNPH No precipitate was observed. Reaction Negative test (-); no aldehyde
remained an orange solution or ketone present
Br2 Reaction turned orange/brown after Br2 No C=C bond or alkyne
reagent (Br2 in Ch2Cl2) present (-)
Chromic acid A dark orange mixture observed No 1° or 2° alcohol (-)
Flame test No greenish flame observed; Reaction Halogen not present (-)*
remained a yellowish flame
* False negative

Spectral Analyses
Any IR, NMR or MS spectra for this compound must be appropriately marked (compound
structure drawn and all important peaks clearly labeled and assigned) and attached to this report.

Espinosa, 1
Espinosa, CHM212B

Infrared Spectral Data:

Absorption (cm-1) &
Intensity (s,m,w)* Structural Assignment
2961 (s) C-H, Sp3 stretching
1459 (m) Maybe C-H2 stretching… variable
* s = strong; m = medium; w = weak

1
H-NMR Spectral Data: (NMR solvent used: CDCl3 )
Chemical Shift Multiplicity # of Protons J (Hz) Structural Assignment
(not ratio) (if needed)
(d) ppm
~3.53 T 2 Ha

~1.57 M 3* Hb, Hc

~0.98 T 3 Hd

* Error in integration/merging of peaks

Compound
Structure:
(use ChemDraw, label
each type of H a
different letter)

13
C-NMR Spectral and Mass Spectral Data: (If obtained, include analysis below and
attach labeled spectra with compound structure drawn and all important peaks clearly assigned.)

N/A

Summary statement regarding logic and reasoning used to arrive at proposed

structure for unknown, be sure to include discussion of other compounds (with
structures) that were considered and cite literature values (e.g., mp, bp, n,
etc.) for your unknown and the comparison compounds.

Espinosa, 2
Espinosa, CHM212B

The analysis began by looking into the 1H-NMRappendix, spectra 1 spectra showing the presence
of a multiplet peak over an array of ppm. This indicated the possibility of the presence of several
atoms being merged into one peak (not integrated separately) and thus there were different
proton types stacked on top of each other. The chemical tests mentioned above were also all
negative, but the 1H-NMR still presented a peak with an integration at ~4PPm which indicates
that there is an electronegative group, pushing the proton peak further down the spectra. Based
on the “Typical Chemical Shifts Table1” the possibility of the protons being attached to a nitro,
oxygen or halogen group was considered. However, the IR(appendix, spectra 2) for unknown denied the
presence of a nitro group (two strong peaks ~1530, 1347)1. Additionally, all chemical tests and
spectra, denied the presence of any other Oxygen containing group, leaving a halogen as the next
most likely answer. Meaning that the result for the halogen (flame) test was a false negative (not
unlikely).
Based on this, and the experimentally measured boiling point (78°C), halogens with a bp
of around that temperature were searched in the Literature2.
The most similar/appropriate compounds (within 5°C from experimental bp and the
carbon attached to the halogen had 2 neighbors– gives a triplet splitting on the 1H-NMR) found
were methallyl chloride, 3-chloro-1-pentene and 1-chlorobutane. Although, it is unsure what the
exact expected splitting would be for the multiplet area, from this, methallyl chloride was
discarded because of the double bond, it only has 3 types of protons, as opposed to the 3+
expected from the unknown 1H-NMR spectra obtained. Additionally, we would expect to see two
singlets in a proton 1H-NMR for such a structure.
Then, choosing between 3-chloro-1-pentene and 1-chlorobutane was a bit difficult since,
although the splitting was not clear, the number of protons expected by the 1H-NMR would be 3.
Thus, the literature3 IR spectra(appendix, spectra 2) 1H-NMR(appendix, spectra 3) and RI (n20D= 1.4023)4, for
1-chlorobutane, were compared to those of the unknown. This revealed an almost exact match
for 1-chlorobutane, whilst it could not be compared to 3-chloro-1-pentene since the literature
spectra was not found. The 1H-NMR spectra for 1-chlorobutane as found in the literature, was
slightly different since 2 smaller multiplets are observed as opposed to the larger one from
unknown 2. However, errors from low resolution (and thus merging of the peaks, could also lead
to smaller areas under them and thus smaller integration and an underestimation of the expected
number of protons. The difference can be due to the fact that the 1H-NMR instruments used to
acquire the data were different in power (300 Hz vs 90Hz) thus the highest one would give a
higher resolution and a merging of the peaks and integration would not be seen at 300 hz. Thus
the literature splitting/integration would just be the one obtained using better instrumentation
In conclusion, a decision was made to prioritize spectral results as compared to literature
over chemical tests since a halogen group is most likely to be present as such chemical tests are

Espinosa, 3
Espinosa, CHM212B

known to yield false results. Although spectral comparison could not be made to
3-chloro-1-pentene most spectral data already correlated to 1-chlorobutane.
Therefore, 1-chlorobutane is assigned as the structure of the unknown #2 as it is supported by the
most experimental data.

STRUCTURES of all compounds discussed.

N/A
Methallyl chloride 1-chlorobutane Methallyl chloride Only 3 discussed

References (Properly cite all literature resources used; include access date for URL citations.)
1) Organic Chemistry Laboratory (CM 211/212) Manual, 2023-2024 Ed., Ed., Chemistry
department, Franklin and Marshall College: Lancaster, PA, 2023
1) Halaides Packet of mp/bp data collected from: CRC Handbook of Chemistry and Physics,
67th Ed., Weast, R. C., Editor, CRC Press: Boca Raton, Fl, 1985.
2) SDBS compound 1287 (https://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi)
Access date: 7th February 2024
4) National Center for Biotechnology Information (2024). PubChem Compound Summary
for CID 8005, N-butyl Chloride. Retrieved February 22, 2024 from
https://pubchem.ncbi.nlm.nih.gov/compound/N-butyl-Chloride.

Espinosa, 4
Espinosa, CHM212B

Appendix:

Spectra 1: IR Unknown compound Spectra 2: 1H-NMR of unknown Compound

Espinosa, 5
Espinosa, CHM212B

3 3
Spectra 3: IR of 1-Chlorobutane (CCl4) Spectra 4: 1H-NMR of 1-Chlorobutane

Espinosa, 6