Chapter 9: Q3P (page 469)
What reaction would acetylene likely to undergo if it were kept at for too long?
Short Answer
When acetylene is kept at for too long, it will decompose into carbon (C) and hydrogen (H) elements.
Chapter 9: Q3P (page 469)
What reaction would acetylene likely to undergo if it were kept at for too long?
When acetylene is kept at for too long, it will decompose into carbon (C) and hydrogen (H) elements.
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Get started for freeOxidative cleavages can help to determine the positions of the triple bonds in alkynes.
(a) An unknown alkyne undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid. Propose a structure for the alkyne.
(b) An unknown alkyne undergoes oxidative cleavage to give the following triacid plus one equivalent of propionic acid. Propose a structure for the alkyne.
Question:Predict the products of the reaction of but-1-yne with the following reagents.
(a)1 equivalent of HCl
(b)2 equivalents of HCl
(c)excess H2 , Ni
(d) H2 , Pd /BaSO4, quinolone
(e)1 equivalent of Br2
(f)2 equivalents of Br2
(g)cold, dilute KMnO4
(h)warm, concd.KMnO4 , NaOH
(i)Na, liquid ammonia
(j) NaNH2
(k) H2SO4/HgSO4, H2O
(l) Sia2BH, then , H2O2,OH-
The hydroboration–oxidation of internal alkynes produces ketones.
(a) When hydroboration–oxidation is applied to but-2-yne, a single pure product is obtained. Determine the structure of this product, and show the intermediates in its formation.
(b) When hydroboration–oxidation is applied to pent-2-yne, two products are obtained. Show why a mixture of products should be expected with any unsymmetrical internal alkyne.
The following functional group interchange is a useful synthesis of aldehydes.
(a)What reagents were used in this chapter for this transformation? Give an example to illustrate this method.
(b)This functional group interchange can also be accomplished using the following sequence.
Propose mechanisms from these steps.
(c) Explain why a nucleophilic reagent such as ethoxide adds to an alkyne more easily than it adds to an alkene.
Deduce the structure of each compound from the information given. All unknown in this problem have molecular formula C8H12.
(a)Upon catalytic hydrogenation, unknown Wgives cyclooctane. Ozonolysis of W,followed by reduction with dimethylsulfide, gives octanedioic acid,HOOC-(CH2) 6-COOH . Draw the structure of W.
(b)Upon catalytic hydrogenation, unknown Xgives cyclooctane. Ozonolysis of X,followed by reduction with dimethyl sulfide, gives two equivalents of butanedial , O =CH -CH2 CH 2-CH = O. Draw the structure of X.
(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethyl sulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.
(d) Upon catalytic hydrogenation, unknown Z gives cis-bicyclo[4.2.0]octane. Ozonolysis of Z, followed by reduction with dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (-CH2-CH2-CHO ) group on C1 and a one-carbon aldehyde (CHO) group on C2. Draw the structure of Z.
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