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The antioxidants BHA and BHT are commonly used as food preservatives. Show how BHA and BHT can be made from phenol and hydroquinone.

Short Answer

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The antioxidants are substances that have the ability to prevent certain cell damages and also protect from free radicals. They are present in fruits and vegetables.

Step by step solution

01

Antioxidants

The antioxidants are substances that have the ability to prevent certain cell damages and also protect from free radicals. They are present in fruits and vegetables.

02

Synthesis of BHA from phenol and hydroquinone

The synthesis of BHA from phenol is carried initially by nitration then alkylation reduction of nitro to an amino group by (Sn + HCl) then diazotization of the amino group to diazonium chloride and finally by the reaction with sodium methoxide BHA is formed.

03

Synthesis of BHT by phenol and hydroquinone

In this phenol undergo nitration followed by 2 times alkylation then undergo reduction with Sn and HCl which then undergo diazotization with sodium nitrite and HCl to form diazonium chloride followed by reaction with sodium ethoxide forms BHT as the desired product.

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Most popular questions from this chapter

In Chapter 14, we saw that Agent Orange contains (2,4,5-trichlorophenoxy) acetic acid, called 2,4,5-T. This compound is synthesized by the partial reaction of 1,2,4,5-tetrachlorobenzene with sodium hydroxide, followed by a reaction with sodium chloroacetate, ClCH2CO2Na.

(a) Draw the structures of these compounds, and write equations for these reactions.

(b) One of the impurities in the Agent Orange used in Vietnam was 2,3,7,8-tetrachlorodibenzodioxin (2,3,7,8-TCDD), often incorrectly called โ€œdioxin.โ€ Propose a mechanism to show how 2,3,7,8-TCDD is formed in the synthesis of 2,4,5-T.

(c) Show how the TCDD contamination might be eliminated, both after the first step and on completion of the synthesis

The antioxidants BHA and BHT are commonly used as food preservatives. Show how BHA and BHT can be made from phenol and hydroquinone.

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

Step 2 of the iodination of benzene shows water acting as a base and removing a proton from the sigma complex. We did not consider the possibility of water acting as a nucleophile and attacking the carbocation, as in an electrophilic addition to an alkene. Draw the reaction that would occur if water reacted as a nucleophile and added to the carbocation. Explain why this type of addition is rarely observed.

The highly reactive triple bond of benzyne is a powerful dienophile. Predict the product of the Dielsโ€“Alder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.

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