CH3 POCl3 pyridine CH2 OH H20 CH3 H3C CH3 Secondary alcohols are often dehydrated in an E2 reaction to give an alkene. Elimination follows Zaitsev's rule to give the more substituted alkene as the major product. Since the reaction occurs via an E2 mechanism, there is no risk of rearrangement of the carbon skeleton as could possibly occur if the elimination occurred via an E1 mechanism with a carbocation intermediate Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Il CI CH3 HO +CI Cl H3C CH3 Нас CH3 Cl Retry Entire Group 8 more group attempts remaining Submit Answer

-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.

2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (ii) What is the type of reaction involved in the formation of compound W? (iii) Identify the major product of the elimination reaction between compound Xand compound Y based on Zaitsev’s rule.

Which one of the statements below is wrong about Zaitsev’s Rule.     a.   None of the above    b.   The Zaitsev’s Rule demonstrate the principle of regioselectivity in elimination reactions   c.   The more substituted alkene is the major product of E1 or E2 elimination     d.   The more substituted alkane product is obtained when a proton is removed from β-carbon that is bonded to the fewest hydrogens      e.   The most stable alkene is generally the major product

Give the structure of the major product formed in each case when the reactant or reactants shown undergo alkene metathesis in the presence of an appropriate ruthenium catalyst.

Show how to prepare each alkyne from the given starting material. In part (c), D indicates deuterium. Deuterium-containing reagents such as BD3, D2O, and CH3COOD are available commercially.

Give reasons for the following: (i) Benzyl chloride is highly reactive towards the SN1 reaction. (ii) 2-bromobutane is optically active but 1-bromobutane is optically inactive. (iii) Electrophilic reactions in haloarenes occur slowly.

Given that an E2 reaction proceeds with anti periplanar stereochemistry, draw the products of each elimination. The alkyl halides in (a) and (b) are diastereomers of each other. How are the products of these two reactions related? Recall from Section 3.2A that C6H5 −is a phenyl group, a benzene ring bonded to another group.

Ethers can often be prepared by SN2 reaction of alkoxide ions, RO*, with alkyl halides. Which of the two possible routes would be the better choice to synthesize the molecule shown below? Explain briefly.

The compound shown below can be synthesised by the reaction of alkyl halide and an alkoxide in the Williamson ether synthesis via an SN2 mechanism. Identify the reagents required and use the plausible mechanism to show the product formation. Also look at the combination of alkyl halide and alkoxide chosen and explain whether or not a good yield of the product is expected.