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문제 18a
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.
문제 18b
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.
(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
문제 19a
Show how you would synthesize the following alcohol by adding Grignard reagents to ethylene oxide.
(a) 2-phenylethanol
문제 19c
Show how you would synthesize the following alcohol by adding Grignard reagents to ethylene oxide.
(c)
문제 20a,b
Acetylide ions also add to ethylene oxide much like Grignard and organolithium reagents. Predict the products obtained by adding the following acetylide ions to ethylene oxide, followed by a dilute acid workup.
(a) HC≡C:–
(b) CH3CH2–C≡C:–
문제 21a
Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.
(a) octane
문제 21c
Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.
(c) trans-oct-3-ene
문제 21d
Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.
(d) cyclopentyl propyl ketone
문제 22a,b,c
Predict the products of the following reactions.
(a) sec-butylmagnesium iodide + D2O
(b) n-butyllithium + CH3CH2OH
(c) isobutylmagnesium bromide + but-1-yne
문제 22d,e
Predict the products of the following reactions.
(d)
(e)
문제 23a
Point out the flaws in the following incorrect Grignard syntheses.
(a)
문제 23b
Point out the flaws in the following incorrect Grignard syntheses.
(b)
문제 23c,d
Point out the flaws in the following incorrect Grignard syntheses.
(c)
(d)
문제 24a
Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(a) CH3–(CH2)8–CHO
문제 24c
Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(c) Ph-COOH
문제 24d
Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(d)
문제 24e
Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(e)
문제 24f
Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(f)
문제 25a
Predict the products you would expect from the reaction of LiAlH4 followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(a) CH3–(CH2)8–CHO
문제 25c
Predict the products you would expect from the reaction of LiALH4 followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(c) Ph-COOH
문제 25d
Predict the products you would expect from the reaction of LiAlH4 followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(d)
문제 25e
Predict the products you would expect from the reaction of LiAlH4 followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(e)
문제 26a
Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
a. heptan-1-ol
문제 26c
Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
c. 2-methylhexan-3-ol
문제 26d
Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
(d)
문제 27
Arrange the following compounds in order of decreasing acidity.
CH3COOH, CH3OH, CH3CH3, CH3SO3H, CH3NH2, CH3SH, CH3C≡CH
문제 28
Give IUPAC names for the following compounds.
문제 29
Authentic skunk spray has become valuable for use in scent-masking products. Show how you would synthesize the major component of skunk spray (3-methylbutane-1-thiol and but-2-ene-1-thiol) from any of the readily available butene or from buta-1,3-diene.
문제 30f,g
Give a systematic (IUPAC) name for each alcohol. Classify each as primary, secondary, or tertiary.
(f)
(g)
문제 31a,b
Give systematic (IUPAC) names for the following diols and phenols.
(a)
(b)
