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Chapter 12: Q22-60E (page 354)

The following synthetic routes are incorrect. What is wrong with each?

Short Answer

Expert verified
  1. The reagent path is incorrect.
  2. Aryl halides cannot participate in SN2 reactions.
  3. The product formed is incorrect.

Step by step solution

01

 Step 1: Reaction (a)

The synthetic route for reaction (a) is wrong.

The given reagents are used in this reaction to carry out bromination for the carbonyl compound. Esters do not undergo bromination with the given reagents.

02

Reaction (b)

The synthetic route for reaction (b) is wrong.

In this reaction, an anion forms an anion of a proton from the reactant (diethyl-2-methyl malonate) by the given base.

In the second step, the anion will attack the phenyl bromide, which is impossible. The nucleophilic attack is impossible on aryl halides because of the double bond between carbon and halide.

03

Reaction (c)

The synthetic route for the reaction (c) is wrong.

The correct sequence and the final product for the given reaction is,

Product formed in reaction (c)

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Most popular questions from this chapter

From what alkyne might each of the following substances have been made? (Green = Cl.)

Question: How would you use infrared spectroscopy to distinguish between thefollowing pairs of constitutional isomers?

(a)

(b)

(c)

CH3≡CCH3ANDCH3COCH2C≡CHCH3COCH≡CHCH3ANDCH3COCH2CH=CH2CH3CH2CHOANDH2C=CHOCH3

Question: 2-Methylpentane (C6H14)has the mass spectrum shown. Which peak

represents? Which is the base peak? Propose structures for fragment

ions of m/z=71, 57, 43, and 29. Why does the base peak have the mass it does?

Grignard reagents undergo a general and very useful reaction with

ketones. Methylmagnesium bromide, for example, reacts with cyclohexanoneto yield a product with the formula C7H14O . What is the structure of this product if it has an IR absorption at 3400 cm-1 ?

Question: Write molecular formulas for compounds that show the following molecular ions in their high-resolution mass spectra, assuming that C, H, N, and O might be present. The exact atomic masses are: 1.00783 (H1), 12.00000 (C12), 14.00307 (N14), 15.99491 (O16).

a)M+=98.0844b)M+=123.0320
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