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Chapter 7: Q11P-c (page 197)

Which member in each of the following sets ranks higher?

-CH2CH2Bror-CH=CH2

Short Answer

Expert verified

-CH=CH2Ranks higher.

Step by step solution

01

E and Z designation

The cis-trans naming system works only for disubstituted alkenes having two substituents other than hydrogen on the double bond. But when trisubstituted and tetra substitution of the double bond is present then the E and Z system is used for describing alkene stereochemistry.

02

Rule for ranking substituents

  • Consider each of the double-bond carbons separately and ranks the two substituents according to the atomic number of the first atom in each. An atom with a higher atomic number will rank higher.
  • If the first atom same then, look at the second, third, or fourth atoms away from the double-bond until the first difference is found.
  • Multiple-bonded atoms are equivalent to the same number of single bonded atoms.
03

Ranking of given groups

As ranking is atomic number dependent, more the atomic number higher will be ranking. So,-CH=CH2 ranks higher as its carbon has two carbon and one hydrogen attached while-CH2CH2Br has carbon with two hydrogens and one carbon attached.

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Most popular questions from this chapter

Draw structures corresponding to the following systematic names:

(a)(4E)-2, 4-Dimethyl-1, 4-hexadiene

(b)cis-3, 3-Dimethyl-4-propyl-1, 5-octadiene

(c)4-Methyl-1, 2-pentadiene

(d)(3E,5Z)-2, 6-Dimethyl-1, 3, 5,7-octatetraene

(e)3-Butyl-2-heptene

(f)trans-2, 2, 5, 5-Tetramethyl-3-hexene

Assign E or Z configuration to the following alkenes:

Predict the major product from addition of HBr to each of the following alkenes:

Rank the carbocations below in terms of increasing stability:

Tamoxifen, a drug used in the treatment of breast cancer, and clomiphene, a drug used in fertility treatment, have similar structures but very different effects. Assign Eor Zconfiguration to the double bonds in both compounds.
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