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Chapter 12: Q23-2 P (page 354)

Using curved arrows to indicate the electron flow in each step, show how the base-catalyzed retro-aldol reaction of 4-hydroxy-4-methyl-2-pentanone takes place to yield 2 equivalents of acetone.

Short Answer

Expert verified

Retro-aldol reaction:A reaction in which 𝛃-hydroxy carbonyl compound is decomposed to give ketone or aldehyde compounds.

Step by step solution

01

attack of base -OH at the hydrogen of alcoholic group:

02

elimination of enolate ion and the formation of the first ketone product:

03

conversion of enolate ion into another ketone compound in the presence of H2O:

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Most popular questions from this chapter

Nitriles, R - C = N , undergo a hydrolysis reaction when heated with

aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH₃CH₂C=N , if it has IR absorptions from 2500-3100cm^-1 and at 1710cm^-1 , and has M⁺ = 74?

Question: Halogenated compounds are particularly easy to identify by their mass

spectra because both chlorine and bromine occur naturally as mixtures

of two abundant isotopes. Recall that chlorine occurs as ³⁵Cl (75.8%)

and ³⁷C (24.2%); and bromine occurs as ⁷⁹Br (50.7%) and ⁸¹Br (49.3%).

At what masses do the molecular ions occur for the following formulas?

What are the relative percentages of each molecular ion?

(a)Bromomethane, CH₃Br

(b)1-Chlorohexane, C₆H₁₃Cl

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 $({}^{1}H)$ , 12.00000 $({}^{12}C)$ , 14.00307 $({}^{14}N)$ , 15.99491 $({}^{16}O)$ .

$a) M^{+} = 98.0844 b) M^{+} = 123.0320$

The infrared spectrum of the compound with the mass spectrum shown below lacks any significant absorption above 3000cm^-1 . There is a prominent peak near 1740cm^-1 and another strong peak near 1200cm^-1 .

Propose a structure consistent with the data.

Question: How might you use IR spectroscopy to distinguish between the following pairs of isomers?

$a) {CH}_{3} {CH}_{2} OH and {CH}_{3} {OCH}_{3} b) cyclohexane and 1 - hexene c) {CH}_{3} {CH}_{2} {CO}_{2} H and {HOCH}_{2} {CH}_{2} CHO$

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