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Organic Chemistry I: Finding Information about Organic Compounds and Spectra, Lab Reports of Organic Chemistry

A part of the che 211 organic chemistry i course materials for fall 2006. It provides instructions on how to find important information about organic compounds, including their molecular formula, mass, melting and boiling points, safety information, and spectra. It also explains how to use various sources such as handbooks, online databases, and the aldrich catalog to find this information.

Typology: Lab Reports

Pre 2010

Uploaded on 08/05/2009

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CHE 211 Organic Chemistry I
Exp01 Chemical Literature & Laboratory Notebooks
Fall 2006 Last Revised 9/5/2006 Page 1 of 3
Relevant Chapters in Zubrick: 2, 3
Introduction
When preparing for work in the laboratory it is essential to know as much as possible about the chemicals and
techniques that you will be using. This is important not only for safety’s sake but also so you can troubleshoot an
experiment while you are performing it. The sources for information are varied and it can be quite intimidating
decided what sources you should use and what information is the most important.
What’s Important and What’s Not?
Usually you perform some sort of chem ical transformation in the laboratory. This is usually given as some sort of
chemical reaction similar to that shown below.
CH
3
COOH
CH
3
COOCH
3
OBr
2
O
Br
HBr
+ +
There are several important features that can help you determine what you need to look up. The major organic
compounds (the compounds with a five-membered ring) are the compounds you’ll want to know the most about.
When looking at the reaction arrow, you will usually find any reagents (CH
3
COOH) above the arrow and any
solvents (CH
3
COOCH
3
) below the arrow. Other minor reagents are shown to the left (Br
2
) of the arrow. Minor
products are shown to the right (HBr) of the arrow. The major organic compounds are the ones you should know
the most about. The other reagents, products, and solvents are important, but prim arily for caution’s sake.
What to Look For and Where to Find It?
There are many details that you should find for all of the compounds listed in a reaction. These include the…
molecular name, formula, and mass
density
melting point and/or boiling point (mp for solids, mp and bp for liquids, and bp for gases)
any important safety information (flamm ability, volatility, toxicity, etc.)
For the major organic compounds, you should look up some additional information related it’s the identification of
the compounds.
index of refraction (for liquids)
mass (MS) spectra
ultraviolet/visible (UV/Vis) spectra
infrared (IR) spectra
nuclear magnetic resonance (NMR) spectra (
1
H or
13
C)
Finding the molecular names, formulas, and masses is a simple matter and there is no need to look anything up.
Other information such as the density, m p, bp, safety information, and index of refraction can be found in one or
more of the common informational books that are available (the Merck Manual, Lange’s Handbook, CRC
Handbook, or the Aldrich Catalog). These days, there are even a couple of online databases that have much of
this information such as eMolecules (http://www.emolecules.com), the NIST WebBook (http://webbook.nist.gov/),
or even ChemFinder (http://www.chemfinder.com/).
Spectra are a bit more difficult to come by. There are several spectral collections available but we don’t have
them here at Front Range. Thankfully, there are two excellent sources for spectra online: the NIST WebBook and
the Spectral Data Base System (http://www.aist.go.jp/RIODB/SDBS/menu-e.html).
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CHE 211 Organic Chemistry I

Exp01 Chemical Literature & Laboratory Notebooks

Fall 2006 Last Revised 9/5/2006 Page 1 of 3

Relevant Chapters in Zubrick: 2, 3

Introduction

When preparing for work in the laboratory it is essential to know as much as possible about the chemicals and techniques that you will be using. This is important not only for safety’s sake but also so you can troubleshoot an experiment while you are performing it. The sources for information are varied and it can be quite intimidating decided what sources you should use and what information is the most important.

What’s Important and What’s Not?

Usually you perform some sort of chemical transformation in the laboratory. This is usually given as some sort of chemical reaction similar to that shown below.

CH 3 COOH CH 3 COOCH 3

O Br 2 O

Br

    • HBr

There are several important features that can help you determine what you need to look up. The major organic compounds (the compounds with a five-membered ring) are the compounds you’ll want to know the most about. When looking at the reaction arrow, you will usually find any reagents (CH 3 COOH) above the arrow and any solvents (CH 3 COOCH 3 ) below the arrow. Other minor reagents are shown to the left (Br 2 ) of the arrow. Minor products are shown to the right (HBr) of the arrow. The major organic compounds are the ones you should know the most about. The other reagents, products, and solvents are important, but primarily for caution’s sake.

What to Look For and Where to Find It?

There are many details that you should find for all of the compounds listed in a reaction. These include the…

  • molecular name, formula, and mass
  • density
  • melting point and/or boiling point (mp for solids, mp and bp for liquids, and bp for gases)
  • any important safety information (flammability, volatility, toxicity, etc.)

For the major organic compounds, you should look up some additional information related it’s the identification of the compounds.

  • index of refraction (for liquids)
  • mass (MS) spectra
  • ultraviolet/visible (UV/Vis) spectra
  • infrared (IR) spectra
  • nuclear magnetic resonance (NMR) spectra (^1 H or 13 C)

Finding the molecular names, formulas, and masses is a simple matter and there is no need to look anything up. Other information such as the density, mp, bp, safety information, and index of refraction can be found in one or more of the common informational books that are available (the Merck Manual, Lange’s Handbook, CRC Handbook, or the Aldrich Catalog). These days, there are even a couple of online databases that have much of this information such as eMolecules (http://www.emolecules.com), the NIST WebBook (http://webbook.nist.gov/), or even ChemFinder (http://www.chemfinder.com/).

Spectra are a bit more difficult to come by. There are several spectral collections available but we don’t have them here at Front Range. Thankfully, there are two excellent sources for spectra online: the NIST WebBook and the Spectral Data Base System (http://www.aist.go.jp/RIODB/SDBS/menu-e.html).

Page 2 of 3 Last Revised 9/5/2006 Fall 2006

How Do You Find It?

Each of the sources of information requires slightly different means of investigation but all of them allows for searching by chemical formula. Avoid searching by chemical name in the handbooks since there are almost an unlimited number of synonyms that you might run into – use a different source to determine the structure first. The online searches are a bit more forgiving if you are 100% certain of the preferred chemical name. Your task is to use several of the literature sources available for searching. You will be assigned a Roman Numeral which corresponds to a specific compound for each part of this exercise.

  1. Using the Handbook of Chemistry and Physics find the a) molecular formula, b) molecular weight, c) boiling point, and d) solubility (list all solvents).

I) 3-cyanobenzoic acid V) 5-methyl-3-hexanone IX) 2,5-ditehylpiperidine II) (±)-3-chlorobutanoic acid VI) chloronitromethane X) pentachloropyridine III) 1-decanethiol VII) 2-iodonaphthalene XI) tridecanal IV) 4-propyl-4-heptanol VIII) nonanoyl chloride XII) N,N′-diethylurea

  1. Using ChemFinder find the a) molecular formula, b) CAS number, and c) either IR or mass spectrum. Print out the spectrum and TAPE it into your laboratory notebook.

I) triphenylcarbinol (IR) V) thiolane (MS) IX) p -cresol (IR) II) benzopincaol (MS) VI) octadecanoic acid (IR) X) benzylamine (IR) III) anthraquinone (IR) VII) menthol (MS) XI) maleic acid (MS) IV) pinane (IR) VIII) coumarin (IR) XII) vanillin (IR)

  1. Using Merck Index find the a) cautions or dangers and b) organic chemistry uses

I) CrO 3 V) CdO IX) LiCℓO 4 II) AℓCl 3 VI) KF X) Na 2 S 2 O 8 III) ZnCl 2 VII) K 2 Cr 2 O 7 XI) NaNH 2 IV) SbCl 3 VIII) Rh XII) Ni(CO) 4

  1. Using Lange’s Handbook of Chemistry find the a) heat of vaporization (∆ H vap) and b) specific heat at 1000 K. Record each with proper units.

I) cyclopentane V) 1-hexene IX) thiacyclopentane II) dibutylsulfide VI) 2-metylbutane X) 1,4-xylene III) diethylamine VII) naphthalene XI) propylbenzene IV) fluorobenzene VIII) thiophenol XII) 1-heptanethiol

  1. Using the Aldrich catalog find the a) molecular formula, b) structural formula, c) boiling point, d) density, e) index of refraction, f) flash point, and g) any associated hazards.

I) benzaldehyde V) isopropyl acetate IX) acrolein II) butyraldehyde VI) piperidine X) benzoyl chloride III) cumene VII) pyrrole XI) 2-ethylhexanoic acid IV) N-ethylaniline VIII) tetrahydronaphthalene XII) tetrahydrofuran

  1. Using eMolecules find the a) molecular structure and b) chemical suppliers.

I) N-cyclohexylhydroxylamine V) acetone IX) trifluoroacetic acid II) 2-methylbiphenyl VI) dimethylsulfoxide X) benzoyl peroxide III) myristicin VII) dichloromethane XI) cyclohexanone IV) 2-methoxyethanol VIII) chloroacetic acid XII) 2-hydrazinoquinoline

  1. Using SDBS find the a) 1 H nmr and b) 13 C nmr spectra.

I) o -ethylnitrobenzene V) 4-nitro- o -phenylenediamine IX) azidobenzene II) 1,3,5-trichlorobenzene VI) L-(–)-α-methylbenzylamine X) allyl phenyl sulfide III) p -chloroanisole VII) diphenoxymethane XI) 3-bromo- o -xylene IV) sec -butylbenzene VIII) 2-iodomesitylene XII) 2,4,6-trimethylstyrene