CHM 237 Lab 15 Report Composition

Activity of 4‐methylcyclohexene via Dehydration of 4‐methylcyclohexanol

Heston Allred

TA: Christine Woolley

Thursday 1: 05-4 pm

Clinical Experiment #10


4-methylcyclohexanol was synthesized to 4-methylcyclohexene using dehydration. 4-methylcyclohexanol was heated to reflux as well as the subsequent distillate (4-methylcyclohexe) was collected. It had been then purified using salt chloride to split up products and an anhydrous stable was then simply added and filtered. The resulting merchandise had a mass of zero. 399 g and a percent yield of 41%. The product was positively discovered and characterized as 4-methylcyclohexene via IR and Br2 test.


To synthesize 4-methylcyclohexene coming from 4-methylcyclohexanol the starting materials can be dried up resulting in the required compound. Intended for dehydration being possible the OH group on the 4-methylcyclohexene must first be changed into H2O through an acid-base reaction utilizing a strong acid solution catalyst such as phosphoric acid solution and sulfuric acid. The H2O will then become the preferred leaving group and leave on its own causing the formation of a carbocation excessively water. The water will remove the acidic hydrogen on the carbocation producing the required alkene along with regenerating the acid catalyst (fig. 2). A period effective approach to collect the 4-methylcyclohexene is usually to heat the response to reflux as it is happening. This allows the item to be segregated from the starting materials by using the hot point disparity between the separated alkene (101-102C) and the beginning alcohol (171-173C). After the distillate is collected any pollutants of normal water and phosphoric acid may be extracted with the help of sodium chloride, drying the resulting organic layer with an desert solid, and filtration. IR of the starting alcohol and the causing alkene may be compared as a means of recognition and portrayal as well as a Br2 test to ensure the correct item was formed.

Procedure and Observations

A mixture of 4-methylcyclohexanol (1. 5mL), 85% phosphoric acid (0. 40mL), and six drops of concentrated sulfuric acidity were heated up to reflux. The mix turned a dark brown upon reaction and darkened with exposure to warmth. Initially the heating temperatures reached 190C but was then simply lowered and maintained in the range of 160-180C until the response mixture halted boiling. The resulting distillate was accumulated and removed. The stillhead the distillate was gathered in was then laundered with salt chloride (1. 0ml) as well as the subsequent mixture was included in the product. This mixture was shaken and aqueous and organic levels were permitted to form. The aqueous level was taken from the organic and the organic and natural dried with anhydrous sturdy and strained through a cotton-plugged pipet. The mass from the product in addition to a percent deliver was identified. An VENTOSEAR was considered and in comparison to the starting material as well as a Br2 test. Benefits and Computations

4-methylcyclohexanol starting mass: 1 ) 164 g

actual 4-methylcyclohexene mass: 0. 399 g

4-methylcyclohexanol molecular weight = 114 g/mol

4-methylcyclohexene molecular weight sama dengan 96 g/mol

Percent yield computations:

% yield = (actual yield/ theoretical yield) 5. 100%

1 ) 164 g 4-methylcyclohexanol 2. 1mol 4-methylcyclohexanol/114 g 2. 1 mol 4-methylcyclohexanol/ one particular mol 4-methylcyclohexene * 96 g/ 1 mol 4-methylcyclohexene = 0. 980 g 4-methylcyclohexene (theoretical yield) 0. 399 g/ 0. 980 g = 0. 407 * completely = forty five. 7% = 41%

Br2 test:

4-methylcyclohexene: 140 drops to reach excessive

4-methylcyclohexanol: 1 drop to achieve excess

Dialogue and Realization

In conclusion, 4-methylcyclohexene was successfully synthesized via dehydration coming from 4-methylcyclohexanol. This result was verified by simply comparing the IR spectra of both equally compounds as well as by performing a Br2 test. The IR spectra for the...


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