Chapter 17: 76P (page 845)
The antioxidants BHA and BHT are commonly used as food preservatives. Show how BHA and BHT can be made from phenol and hydroquinone.
Chapter 17: 76P (page 845)
The antioxidants BHA and BHT are commonly used as food preservatives. Show how BHA and BHT can be made from phenol and hydroquinone.
All the tools & learning materials you need for study success - in one app.
Get started for freeIn 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 โdioxin.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 DielsโAlder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.
What do you think about this solution?
We value your feedback to improve our textbook solutions.