Chapter 14: Q7P (page 718)
Propose a fragmentation to account for each numbered peak in the mass spectrum of n-butyl isopropyl ether.
Chapter 14: Q7P (page 718)
Propose a fragmentation to account for each numbered peak in the mass spectrum of n-butyl isopropyl ether.
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Get started for freeQuestion: Both LiAlH4and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that become protonated in an aqueous workup). Those alkoxides can react with 1o or methyl alkyl halides or tosylates to give ethers. Show how the following ethers can be formed in this two -step process. As starting materials, you may use any reactants containing 8carbons or fewer.
(Another true story) An organic lab student carried out the reaction of methyl magnesium iodide with acetone (CH3COCH3), followed by hydrolysis. During the distillation to isolate the product, she forgot to mark the vials she used to collect the fractions. She turned in a product of formula C4H10Othat boiled at 350C.The IR spectrum showed only a weak O-Hstretch around 3300 cm-1, and the mass spectrum showed a base peak at m/z 59.The NMR spectrum showed a quartet (J = 7Hz) of area 3at δ1.3Propose a structure for this product, explain how it corresponds to the observed spectra, and suggest how the student isolated this compound.
Show how you would use a protecting group to convert 4-bromobutan-1-ol to hept-5-yn-1-ol.
Show how you would use the Williamson ether synthesis to prepare the following ethers. You may use any alcohols or phenols as your organic starting materials.
Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule.
(a) Draw the enantiomers of propylene oxide.
(b) Propose a mechanism for the acid-catalyzed hydrolysis of pure .
(c) Propose a mechanism for the base-catalyzed hydrolysis of pure .
(d) Explain why the acid-catalyzed hydrolysis of optically active propylene oxide gives a product with lower enantiomeric excess and a rotation opposite that of the product of the base- catalyzed hydrolysis.
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