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Chapter 8: Q8-2P. (page 222)

Question: How many alkene products, including E, Z isomers, might be obtained by dehydration of 3-methyl-3-hexanol with aqueous sulfuric acid?

Short Answer

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Answer

The five alkene products formed are,

Step by step solution

01

Dehydration with aqueous sulfuric acid

The dehydration of alcohol in acid catalyst H2SO4removes water from the alcohol and forms an alkene product. H2SO4 Is a good dehydrating agent and is very good at removing water from the compounds.

02

The formation of alkene products

When 3-methyl-3-hexanol is dehydrated with aqueous H2SO4, it removes water (OH and H group). The five alkene products obtained are E/Z-3-Methyl-3-hexene, E/Z-3-Methyl-2-hexene and 2-Ethyl-1-pentene.

Formation of alkene products

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Most popular questions from this chapter

Reaction of 2-methylpropene with CH3OH in the presence of H2SO4

catalyst yields methyl tert-butyl ether, CH3OC(CH3)3, by a mechanism

analogous to that of acid-catalyzed alkene hydration. Write the mechanism,

using curved arrows for each step.

伪-Terpinene,C10H16is a pleasant-smelling hydrocarbon that has been isolated from oil of marjoram. On hydrogenation over a palladium catalyst,伪-terpinene reacts with two molar equivalentsH2to yield a hydrocarbon, C10H20.On ozonolysis, followed by reduction with zinc and acetic acid,伪-terpinene delivers two products, glyoxal, and 6-methyl-2,5- heptane dione.

(a) How many degrees of unsaturation does伪-terpinene have?

(b) How many double bonds and how many rings does it have?

(c) Propose a structure for伪-terpinene

When a single alkene monomer, such as ethylene, is polymerized, the product is a homopolymer. If a mixture of two alkene monomers is polymerized, however, a copolymer often results. The following structure represents a segment of a copolymer called Saran. What two monomers were copolymerized to make Saran?

Question: In planning the synthesis of one compound from another, it鈥檚 just as important to know what not to do as to know what to do. The following reactions all have serious drawbacks to them. Explain the potential problems of each.

Poly (vinyl pyrrolidone), prepared from N-vinylpyrrolidone, is used in cosmetics and as a synthetic substitute for blood. Draw a representative segment of the polymer.
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