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Chapter 20: Q58P (page 1038)

When LiAlH4reduces 3 - methylcyclopentanone , the product mixture contains 60%cis- 3 - methylcyclopentanol and40%trans- 3 - methylcyclopentanol . Use your models, and make three-dimensional drawings to explain this preference for the cis isomer

Short Answer

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3 - methylcyclopentanonecis- 3 - methylcyclopentanoltrans- 3 - methylcyclopentanoltrans- 3 - methylcyclopentanol

Step by step solution

01

Cis- and trans-isomers

Cis- and trans-isomerism can be used only for the compounds in which two doubly bonded carbon atoms are having similar atoms or groups. When the similar atoms or groups lie on the same side, it is called as cis-isomer and when similar atoms or groups lie on the opposite sides, it is called as trans-isomer.

02

Explanation

Lithium aluminum hydride (LiAlH4 ) is considered to be a strongest reducing agent. Hydride anion ( ) when added to an aldehyde or a ketone gives an alkoxide ion which on protonation gives the alcohol.

3 - methylcyclopentanonecis- 3 - methylcyclopentanoltrans- 3 - methylcyclopentanol

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Most popular questions from this chapter

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a)methyl salicylate

(b) methyl formate (32°C)

(c) ethyl phenylacetate

The reaction of tert-butyl alcohol with concentrated HCl goes by the SN1 mechanism. Write a mechanism for this reaction.

Most of the Fischer esterification mechanism is identical with the mechanism of acetal formation. The difference is in the final step, where a resonance-stabilized carbocation loses a proton to give the ester. Write mechanisms for the following reactions, with the comparable steps directly above and below each other. Explain why the final step of the esterification (proton loss) cannot occur in acetal formation, and show what happens instead.

(a) How many asymmetric carbon atoms are there in an aldotetrose? Draw all the aldotetrose stereoisomers.

(b) How many asymmetric carbon atoms are there in a ketotetrose? Draw all the ketotetrose stereoisomers.

(c) How many asymmetric carbon atoms and stereoisomers are there for an aldohexose? For a ketohexose?

Q.13Most of the Fischer esterification mechanism is identical with the mechanism of acetal formation. The difference is in the final step, where a resonance-stabilized carbocation loses a proton to give the ester. Write mechanisms for the following reactions, with the comparable steps directly above and below each other. Explain why the final step of the esterification (proton loss) cannot occur in acetal formation, and show what happens instead.
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