From: "Gregory, Elizabeth A (egregory)" <egregory**At_Symbol_Here**BROCKPORT.EDU>
Subject: Re: [DCHAS-L] [NAOSMM] Experience with 4-methylcyclohexene Lab
Date: Sun, 4 Nov 2018 19:12:33 +0000
Reply-To: ACS Division of Chemical Health and Safety <DCHAS-L**At_Symbol_Here**PRINCETON.EDU>
Message-ID: DM5PR20MB1385B700E2994856656D6D9FD8C90**At_Symbol_Here**
In-Reply-To <1ab0a5a0-d654-0778-195d-49cb0bf35a6e**At_Symbol_Here**>

We don't do this particular one. Instead, we dehydrate a pentanol (I think it's 4-methyl-2-pentanol?) using sulfuric and (I think?) glacial acetic acid. No phosphoric acid whatsoever. We also do this on a microscale level. I'm pretty sure we do this in a conical vial with a condenser on the top. The students analyze the products by GC, which we autosample.

Does it stink? Oh yes. Those pentenes are truly offensive. We minimize this by having them perform the workup in a test tube that is immersed in an ice bath, and they immediately rinse all glassware that came into contact with them with acetone into the waste bottle. At the most, you get a quick whiff of it and then it's gone.


Elizabeth Gregory

Laboratory Manager

Department of Chemistry and Biochemistry

The College at Brockport

221 Smith Hall

Brockport, NY 14420

(585) 395-2210


From: NAOSMM <naosmm-bounces**At_Symbol_Here**> On Behalf Of Samuella Sigmann
Sent: Wednesday, October 31, 2018 1:18 PM
To: Wilhelm, Monique <mwilhelm**At_Symbol_Here**>; naosmm**At_Symbol_Here**; DCHAS-L**At_Symbol_Here**PRINCETON.EDU
Subject: Re: [NAOSMM] Experience with 4-methylcyclohexene Lab


Hi Monique - I can't help answer your question, but we do do this experiment.  Lots of waste as well.  We disperse chemicals in a reagent hood and all our students work in hoods, so I guess we are fortunate in that way.

Looking forward to the answers.

On 10/31/2018 1:15 PM, Wilhelm, Monique wrote:

Hi everyone,
I am reaching out to see if anyone has experience with the dehydration of 4-methylcyclohexanol to 4-methylcyclohexene lab in the Pavia et al lab textbook. The reaction seems to call for an awful lot of H2SO4 in addition to H3PO4 and is giving off several noxious odors.  I would like to recommend getting rid of the H2SO4 but am concerned about whether this may cause unwanted organophosphates to be produced.  I am concerned as I cannot figure out what kind of byproduct or decomp products we may be getting.  
Does anyone have any thoughts on this?  I am not an organic chemist, so maybe I am just overthinking this one too much.
Monique Wilhelm, M.S., NRCC Certified CHO
ACS CHAS Secretary|2017 CERM E. Ann Nalley Award Recipient
Laboratory Manager|Adjunct Lecturer|Chemistry Club Advisor
Department of Chemistry & Biochemistry|University of Michigan-Flint




We, the willing, led by the unknowing, are doing the impossible for the ungrateful. We have done so much, for so long, with so little, we are now qualified to do everything with nothing. Teresa Arnold paraphrased from Konstantin Josef Jirec˙ek (1854 - 1918)


Samuella B. Sigmann, MS, NRCC-CHO

Senior Lecturer/Safety Committee Chair/Director of Stockroom

A. R. Smith Department of Chemistry

Appalachian State University

525 Rivers Street

Boone, NC 28608

Phone: 828 262 2755

Fax: 828 262 6558

Email: sigmannsb**At_Symbol_Here**


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