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Chapter 19: Q19-5P (page 613)

Treatment of an aldehyde or ketone with cyanide ion (:-C≡N), followed by protonation of the tetrahedral alkoxide ion intermediate, gives a cyanohydrin.

Show the structure of the cyanohydrin obtained from cyclohexanone.

Short Answer

Expert verified

Cyanohydrin formation occurs by adding “nucleophile cyanide (CN)” to the carbonyl carbon of aldehyde/ketone.

The formation of cyanohydrin leads to the following changes:

  • The formation of an alkoxide ion intermediate by pushing an electron pair from the C=O bond to the oxygen atom.
  • Carbonyl carbon hybridization change from sp2→sp3 .

Step by step solution

01

Step-by-Step SolutionStep 1:Formation of Cyanohydrin

Cyanohydrin formation occurs by adding “nucleophile cyanide (CN)” to the carbonyl carbon of aldehyde/ketone.

The formation of cyanohydrin leads to the following changes:

  • The formation of an alkoxide ion intermediate by pushing an electron pair from the C=O bond to the oxygen atom.
  • Carbonyl carbon hybridization change from sp2→sp3 .
02

Step 2:Structure of Cyanohydrin formed

The nucleophile addition of cyanide ion on the carbonyl carbon of cyclohexanone (ketone) occurs in the following steps:

  • Cyanide anion adds to the positively polarized carbon to form a tetrahedral intermediate.
  • This intermediate is protonated to yield the cyanohydrin.

The formation and structure of the cyanohydrin are shown as follows:

Structure of cyanohydrin formed

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Most popular questions from this chapter

Compound B is isomeric with A (Problem 19-79) and shows an IR peak at 1715 cm-1. The 1HNMR spectrum of B has peaks at 2.4 δ(1 H, septet, J = 7 Hz), 2.1 δ(3 H, singlet), and 1.2 δ(6 H, doublet, J =7 Hz). What is

the structure of B?

What is the stereochemistry of the pyruvate reduction shown in Figure 19-12? Does NADH lose its pro-R or pro-S hydrogen? Does addition occur to the Si face or Re face of pyruvate? (Review Section 5-11.)

Acid-catalyzed dehydration of 3-hydroxy-3-phenylcyclohexanone leads to an unsaturated ketone. What possible structures are there for the product? At what position in the IR spectrum would you expect each to absorb? If the actual product has an absorption at 1670 cm-1, what is its structure?

Propose structures for ketones or aldehydes that have the following H1NMR spectra:

(a)C10H12O

localid="1656491160287" IR:1710cm-1

(b) localid="1656491164732" C6H12O3

localid="1656491168876" IR:1715cm-1

Choose the structure that best fits the IR spectrum shown.
See all solutions

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