Chapter 11: Q18P (page 560)
Write balanced equations for the three preceding reactions.
Short Answer
(a)
(b)
(c)
Chapter 11: Q18P (page 560)
Write balanced equations for the three preceding reactions.
(a)
(b)
(c)
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Get started for freeUnknown Q is determined to have a molecular formula of C6H12O. Q is not optically active, and passing it through a chiral column does not separate it into enantiomers. Q does not react with Br2, nor with cold, dilute KMnO4 , nor does it take up H2under catalytic hydrogenation. Heating of Q with H2SO4 gives product R, of formula C6H10, which can be separated into enantiomers. Ozonolysis of a single enantiomer of R produces S, an acyclic, optically active ketoaldehyde of formula C6H10O2. Propose structures for compounds Q, R, and S, and show how your structures would react appropriately to give these results.
Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr3, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4 dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.
Predict the major products of the following reactions.
(a)ethyl tosylate+potassium tert-butoxide
(b) isobutyl tosylate + NaI
(c) (R)-2-hexyl tosylate + NaCN
(d) the tosylate of cyclohexylmethanol +excess NH3
To practice working through the early parts of a multistep synthesis, devise syntheses of
(a) pentan-3-one from alcohols containing no more than three carbon atoms.
(b) 3-ethylpentan-2-one from compounds containing no more than three carbon atoms.
Alcohols combine with ketones and aldehydes to form interesting derivatives, which we will discuss in Chapter 18. The following reactions show the hydrolysis of two such derivatives. Propose mechanisms for these reactions.
(a)
(b)
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