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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: Show the products you expect when each compound reacts with NBS with light shining on the reaction.

b)

Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.

(a) Predict the products formed when phosgene reacts with excess propan-1-ol.

(b) Predict the products formed when phosgene reacts with 1 equivalent of ethanol, followed by 1 equivalent of aniline.

(c) Iso-butyloxycarbonyl chloride is an important reagent for the synthesis of peptides and proteins. Show how you would use phosgene to synthesize iso-butyloxycarbonyl chloride.

Isobutyloxycarbonyl chloride

Question: Oxidation of primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

  1. Show how you would use acid-base extraction to purify the pentanal.
  2. Which of the expected impurities cannot be removed from pentanal by acid-base extractions? How would you remove this impurity?

Question: Give both IUPAC names and common names for the following compounds.

(a) phCH2COOH

(b) phCO2Na

(c) (CH3)2 CHCHCICOOH

(d) HOOC (CH2)4CO2H

(e) (CH3)2 CHCH2COOK

(f) CH3 CH(NH2) COOH

(g)

(h)

(i)

Question: Draw the structures of the following compounds.

  1. propanoic acid
  2. phthalic acid
  3. calciumformate
  4. succinic acid
  5. dibromoacetic acid
  6. acetylsalicylate (aspirin)
  7. zincdecanoate (athlete's-foot powder)
  8. potassium benzoate (a food preservative)
  9. potassium fluoroacetate
See all solutions

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