Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 5.2, Problem 5.4P
Interpretation Introduction

Interpretation:

Given alkene whether has cis, trans isomerization has to be identified and if present, the structure of trans isomer has to be drawn

Concept Introduction:

IUPAC nomenclature:

  • • Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name.
  • • Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers.
  • • Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix.
  • • Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose.

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers.

Trans configuration: In trans configuration, carbon atoms present in the main chain are placed on opposite sides of the carbon-carbon double bond.

Cis configuration: In cis configuration, carbon atoms present in the main chain are placed on same sides of the carbon-carbon double bond.

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TRUE OR FALSE (a) Both ethylene and acetylene are planar molecules. (b) An alkene in which each carbon of the double bond has two different groups bonded to it will show cis-trans isomerism. (c) Cis-trans isomers have the same molecular formula but a different connectivity of their atoms. (d) Cis-2-butene and trans -2-butene can be interconverted by rotation about the carbon–carbon double bond. (e) Cis-trans isomerism is possible only among appropriately substituted alkenes. (f) Both 2-hexene and 3-hexene can exist as pairs of cis-trans isomers. (g) Cyclohexene can exist as a pair of cis-trans isomers. (h) 1-Chloropropene can exist as a pair of cis-trans isomers.
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Draw a structure for each compound (includes old and new names).(a) 3-methylpent-1-ene
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