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Chapter 9: Q15. (page 350)

Question: Show how a 1,2-shift forms a more stable carbocation from each intermediate.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Step-by-Step Solution Step 1: Carbocation

The positive charge on the carbon results in the formation of a carbocation. It is of four types. The order of stability of carbocation is mentioned below.

3°>2°>1°

02

Shifting of hydride or methyl

a. The shifting of hydride is shown below.

Formation of stable carbocation

b. The shifting of hydride is shown below.

Formation of stable carbocation

c. The shifting of methyl is shown below

Formation of stable carbocation

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Most popular questions from this chapter

Question: Epoxides are converted to allylic alcohols with non-nucleophilic bases such as lithiumdiethylamide [LiNCH2CH32] . Draw a stepwise mechanism for the conversion of1,2-epoxycyclohexane to cyclohex-2-en-1-ol with this base. Explain why a strong bulky basemust be used in this reaction.

Question: Answer each question using the ball-and-stick model of compound A.

a. Give the IUPAC name for A, including R,Sdesignations for stereogenic centers.

b. Classify A as a 1°,2°,3°alcohol.

c. Draw a stereoisomer for A and give its IUPAC name.

d. Draw a constitutional isomer that contains an OH group and give its IUPAC name.

e. Draw a constitutional isomer that contains an ether and give its IUPAC name.

f. Draw the products formed (including stereochemistry) when A is

treated with each reagent: [1] NaH; [2] ; [3] , pyridine;

[4] HCl; [5] ,pyridine; [6] TsCl, pyridine.

Question: Explain the following observation. When 3-methylbutan-2-ol is treated with HBr, a single alkylbromide is isolated, resulting from a 1,2-shift. When 2-methylpropan-1-ol is treated with HBr, no rearrangement occurs to form an alkyl bromide.

Question:(a) What reaction conditions are needed to convert (R)-2-ethyl-2-methyloxirane to (R)-2-methylbutane-1,2-diol?

(b) What reaction conditions are needed to convert (R)-2-ethyl-2-methyloxirane to (S)-2-methylbutane-1,2-diol?

Question: Why is the boiling point of propane-1,3-diol higher than the boiling point of propane-1,2-diol [HOCH2CHOHCH3]role="math" localid="1648635549686" (215°Cvs185°C)? Why do both diols have a higher boiling point than butan-1-ol CH3CH2CH2CH2OH,118°C ?
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