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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

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.

a)

b)

c)

Question: Arrange each group of compounds in order of increasing basicity.

  1. CH3COO-,CICH2C00- , and PhO-
  2. sodium acetylide, sodium amide, and sodium acetate
  3. sodium benzoate, sodium ethoxide, and sodium phenoxide
  4. pyridine, sodium ethoxide, and sodium acetate

The following NMR spectra correspond to the compound of formula (A) C9H10O2, (B) C4H6O2, C6H10O2 . Propose structure, and show how it is consistent with the observed absorptions.

When pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:

(a)Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetric carbon atom. (Using your models may be helpful.)

(b)Determine the relationship between the two stereoisomers you have drawn.
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