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Chapter 9: Q18. (page 355)

Question: Draw the products of each reaction, indicating the stereochemistry around any stereogenic centers.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Step-by-Step Solution Step 1: Substitution reaction

Different types of alcohols undergo SN2 or SN1 in the presence of HX, such as the treatment of primary alcohol with HX followed by SN2 and that of the tertiary alcohol followed by SN1.

02

Formation of the product

a. The given compound is a primary alcohol. The reaction of it with HI results in the formation of the inversion product, as shown below.

Formation of the product in a

b. The given compound is a tertiary alcohol. The reaction of it with HBr results in the formation of a racemic mixture, as shown below.

Formation of the product in b

c. The given compound is a tertiary alcohol. The reaction of it with HCl results in the formation of a racemic mixture, as shown below

Formation of the product in c

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Most popular questions from this chapter

Question: Draw the product formed when each ether is treated with two equivalents ofHBr.

a.


b.


c.

Question: Name each thiol.

a.

b.

Question:Rearrangements can occur during the dehydration of alcohols even though no carbocation is formed-that is, a 1,2-shift occurs as the C-O+H2 bond is broken, forming a more stable 2°or3°carbocation, as shown. Using this information, draw a stepwise mechanism that shows how CH3CH2CH2CH2OH is dehydrated with H2SO4to form a mixture of CH3CH2CH=CH2and the cis and trans isomers of CH3CH=CHCH3. We will see another example of this type of rearrangement in Section 18.5C.

Question: Draw two different routes to each of the following ethers using a Williamson ether synthesis. Indicate the preferred route (if there is one).

a.

b.

c.

Question: Although alcohol V gives a single alkene W when treated with POCl3 and pyridine, three isomeric alkenes (X–Z) are formed on dehydration with H2SO4. Draw a stepwise mechanism for each reaction and explain why the difference occurs.
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