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Chapter 7: PROBLEM 7.47 (page 291)

Question: Which of the following molecules contain a good leaving group?

a.

b.

c.

d.

Short Answer

Expert verified

ANSWER

The answer is option (d).

Step by step solution

01

Leaving group

The leaving group in an organic molecule is the one that will break its bond with carbon easily and can have individual stable existence after that.

02

Explanation

Among the given substrates, the leaving group is as follows:

  • In compound a, it is -OH .
  • In compound b, it is Cl-.
  • In compound c, there is no leaving group.
  • In compound d, the leaving group is H2O .

Among all, the compound containing H2Ois highly stable. So, the answer is option (d).

A molecule that contains a good leaving group

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Most popular questions from this chapter

Draw a stepwise mechanism for the following reaction that illustrates how two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under reaction conditions, even though it is a 1°alkyl halide.

Question: Identify the stronger nucleophile in each pair of anions.

a. Br- or Cl- in a polar protic solvent.

b. OH-or Cl- in a polar aprotic solvent.

c. HS- or F- in a polar protic solvent.

Question: When a single compound contains both a nucleophile and a leaving group, an intramolecular reaction may occur. With this in mind, draw the product of the following reaction.

Question: An sp3 hybridized C-Cl bond is more polar than a sp2 hybridized C-Cl bond. (a) Explain why this phenomenon arises. (b) Rank the following compounds in order of increasing boiling point.

Question: In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur, and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1-phenylpropan-1-ol. a. Calculate how much of each enantiomer is present using the given optical rotation data. b. Which product predominates—the product of inversion or the product of retention of configuration? c. Suggest an explanation for this phenomenon.
See all solutions

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