Alkene From Cyclohexanol
Alkene Synthesis from Alcohol:
Preparation of Cyclohexene From Cyclohexanol
5/29/14
Abstract: A 42.89% yield cyclohexene was successfully synthesized from 10.0 mL cyclohexanol by unimolecular elimination (E1) through the dehydration of cyclohexanol and confirmed via a bromine test and the IR spectra.
Introduction:
Alkenes are hydrocarbons that have carbon–carbon double bonds and are one of the many functional groups in organic molecules. Alkenes are sp2 hybridized and are unsaturated because two of their hydrogen’s are missing from the saturated alkane formula (CnH2n+2). Typically alkenes are synthesized by elimination reactions, however, organic molecules can also undergo substitution reactions …show more content…
Sn2 is undergone by primary and secondary substrates only preferable in a polar protic solvent with a relatively good nucleophile while Sn1 is undergone by secondary and tertiary substrates only preferably in a polar protic solvent with a poor nucleophile. Additionally, tertiary substrates are better than secondary substrates for Sn1 because of the stabilization of the carbocation with the polar protic solvent increasing the stability of the carbocation. There is always competition between substitution and elimination reactions depending on the conditions of the reaction. Under normal circumstances Sn1 is always accompanied by E1 as the minor product but E1 products can be favored by changing the conditions of the reaction such as higher temperatures, which always favor E1 …show more content…
The acid used in this experiment was 85% phosphoric acid and the alcohol was cyclohexanol. The phosphoric acid is a catalyst and as such increased the rate of reaction but did not affect the overall stoichiometry. In this reaction, as the alcohol and acid were heated, alkene and water were produced and co-distilled into a collection vial. As in any distillation, unless precautions are taken, some of the product would have been lost as hold-up in the apparatus. Hold-up would result in a reduced yield of product. To overcome this problem and to ensure that a maximum amount of product is distilled, a higher boiling "chaser" solvent was added to the distillation flask and the distillation is continued until the temperature rose well over the BP of cyclohexene. At this point it was assumed that all product has distilled into the collection
Preparation of Cyclohexene From Cyclohexanol
5/29/14
Abstract: A 42.89% yield cyclohexene was successfully synthesized from 10.0 mL cyclohexanol by unimolecular elimination (E1) through the dehydration of cyclohexanol and confirmed via a bromine test and the IR spectra.
Introduction:
Alkenes are hydrocarbons that have carbon–carbon double bonds and are one of the many functional groups in organic molecules. Alkenes are sp2 hybridized and are unsaturated because two of their hydrogen’s are missing from the saturated alkane formula (CnH2n+2). Typically alkenes are synthesized by elimination reactions, however, organic molecules can also undergo substitution reactions …show more content…
Sn2 is undergone by primary and secondary substrates only preferable in a polar protic solvent with a relatively good nucleophile while Sn1 is undergone by secondary and tertiary substrates only preferably in a polar protic solvent with a poor nucleophile. Additionally, tertiary substrates are better than secondary substrates for Sn1 because of the stabilization of the carbocation with the polar protic solvent increasing the stability of the carbocation. There is always competition between substitution and elimination reactions depending on the conditions of the reaction. Under normal circumstances Sn1 is always accompanied by E1 as the minor product but E1 products can be favored by changing the conditions of the reaction such as higher temperatures, which always favor E1 …show more content…
The acid used in this experiment was 85% phosphoric acid and the alcohol was cyclohexanol. The phosphoric acid is a catalyst and as such increased the rate of reaction but did not affect the overall stoichiometry. In this reaction, as the alcohol and acid were heated, alkene and water were produced and co-distilled into a collection vial. As in any distillation, unless precautions are taken, some of the product would have been lost as hold-up in the apparatus. Hold-up would result in a reduced yield of product. To overcome this problem and to ensure that a maximum amount of product is distilled, a higher boiling "chaser" solvent was added to the distillation flask and the distillation is continued until the temperature rose well over the BP of cyclohexene. At this point it was assumed that all product has distilled into the collection