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Preparation




AROMATIC HYDROCARBONS.

Lekture 3

Lek: Alimkulova E. J.

 

Benzene is the first and principal member of the series of aromatic hydrocarbons, and exhibits the unique characteristics of all members of this series/ Benzene was first isolated by Michael Faraday in 1825? But it was ten years before its molecular formula was determined to be C6H6. During the next twenty years chemists were plagued with the problem of its structure. Though the molecular formula implied a high degree of unsaturation. its chemical properties were not at all like alkenes or akynes. It did not react with bromine and potassium permanganate, though under special condition, and special catalysts, it could made to react with bromine in a substitution (not addition) process.

In 1865, Germam chemist Frederick Kekule proposed that the benzene molecule was a cyclic, hexagonal, planar structure of six carbon atoms joined with alternating single and double bonds and that each carbon atom was joined to a single hydrogen atom.

 

Kekule structure

 

Benzene is a colorless liquid at room temperature, It is in soluble in water but soluble in most no polar organic liquids. Though benzene and its derivative were are one time called aromatic because there generally pleasant odors, to day the term has taken on a new meaning which describes the unique benzene-like bonding in the six member-ring.

 

Write formulas: toluene, phenol, aniline, para-diclorbenzene, naphthal ene, phenantrene.

Aromatic compounds can undergo substitution reactions in which an atom or group or atomics substituted for a hydrogen in the ring. Unlike in the substitution reactions of the alkanes, those involving aromatic compounds usually require a specialist catalyst but do not require ultraviolet light or elevated temperatures.

If bromine is added to a solution of benzene, no reaction will occur. However, if a small amount of solid iron (III) chloride (a catalyst) is added to the mixture, the bromine substitution will take place and the red-brown color of molecular bromine will disappear as it is consumed.

FeCl3

C6H6 + Br2 → C6H5Br + HBr

Benzene Brombenzene

С6H6 + HONO2 → C6H5NO2 + H2O

Benzene Nitric acid Nitrobenzene

C6H5Cl + 2Na + ClCH3 → C6H5CH3 + 2NaCl

 

C6H5COONa + NaOH → C6H6 + Na2CO3

 

3 HC≡CH → C6H6

 

Glossary:

Aromatic hydrocarbons - ароматты комiсутектер – ароматические

углеводороды

Benzene - бензол - бензол

Toluene – толуол – толуол

Reaction of the substitution – орын басу реакциясы – реакция замещения

A catalyst - катализатор – катализатор

Mixture – қоспа – смесь

References:

Frederick A. Bettelheim, Joseph M. Landesberg. Organic Chemistry

Charles H.Yenrickson, Larry C. Byrd, Norman W. Hunter. Organic Chemistry.

Cтепаненко Б.Н. Органическая химия.

Грандберг А.Г. Основы органической химии.

Ахметов А. Органикалык химия.

 




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