Chapter 10: Q44P (page 538)
Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.
a)
b)
c)
Short Answer
a)
b)
c)
Chapter 10: Q44P (page 538)
Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.
a)
b)
c)
a)
b)
c)
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Get started for freeShow how to make these deuterium-labeled compounds, using CD3MgBrand D2Oas your sources of deuterium, and any non-deuterated starting materials you wish.
(a) CH3CH(OD)CD3(b) CH3C(OH)(CD3)2 (c) CD3CH2CH2O(d) Ph(CD3)2COD
Geminal diols, or 1,1-diols, are usually unstable, spontaneously losing water to give carbonyl compounds. Therefore, germinal diols are regarded as hydrated forms of ketones and aldehydes. Propose a mechanism for the acid-catalyzed loss of water from propane-2,2-diol to give acetone.
Show how you would synthesize each tertiary alcohol by adding an appropriate Grignard reagent to a ketone.
(a)3-phenylhexane-3-ol (3ways)
(b) Ph3 COH
(c) 1-ethylcyclopentanol
(d) 2-cyclopentylpentan-2-ol
A formate ester, such as ethyl formate, reacts with an excess of a Grignard reagent to give (after protonation) secondary alcohols with two identical alkyl groups.
a. Propose a mechanism to show how the reaction of ethyl formate with an excess of allylmagnesium bromide gives, after protonation, hepta-1,6-dien-4-ol.
b. Show how you would use reactions of Grignard reagents with ethyl formate to synthesize the following secondary alcohols.
i. pentan-3-ol
ii. diphenylmethanol
iii. trans, trans-nona-2,7-dien-5-ol
Many hunting dogs enjoy standing nose-to-nose with a skunk while barking furiously, oblivious to the skunk spray directed toward them. One moderately effective way of lessening the amount of odor is to wash the dog in a bath containing dilute hydrogen peroxide, sodium bicarbonate, and some mild dish detergent. Use chemical reactions to describe how this mixture helps to remove the skunk spray from the dog. The two major components of skunk oil are 3-methylbutane-1-thiol and but-2-ene-1-thiol.
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