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Write structural formulas for all the alkene products that could reasonably be formed from each of the following compounds under the indicated reaction conditions. Where more than one alkene is produced, specify the one that is the major product. (f) 2,4-Dimethyl-3-pentanol (sulfuric acid, 120°C)
 
 

 

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Write structural formulas for all the alkene products that could reasonably be formed from each of the following compounds under the indicated reaction conditions. Where more than one alkene is produced, specify the one that is the major product. (e) 3-Iodo-2,4-dimethylpentane (sodium ethoxide, ethanol, 70°C)

 

 

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Write structural formulas for all the alkene products that could reasonably be formed from each of the following compounds under the indicated reaction conditions. Where more than one alkene is produced, specify the one that is the major product. (d) 2,3-Dimethyl-2-butanol (phosphoric acid, 120°C)

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Write structural formulas for all the alkene products that could reasonably be formed from each of the following compounds under the  indicated reaction conditions. Where more than one alkene is produced, specify the one that is the major product. (c) 3-Methyl-3-pentanol (sulfuric acid, 80°C)
 

 

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Write structural formulas for all the alkene products that could reasonably be formed from each of the following compounds under the indicated reaction conditions. Where more than one alkene is produced, specify the one that is the major product. (b) 1-Methylcyclopentyl chloride (sodium ethoxide, ethanol, 70°C)
 

 

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Write structural formulas for all the alkene products that could reasonably be formed from each of the following compounds under the indicated reaction conditions. Where more than one alkene is produced, specify the one that is the major product. (a) 1-Bromo-3,3-dimethylbutane (potassium tert-butoxide, tert-butyl alcohol, 100°C)
 

 

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How many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case.  (h) 3-Bromo-2,2-dimethylbutane
 

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How many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case.  (g) 3-Bromo-3-methylpentane

 

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How many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case. (e) 2-Bromo-3-methylpentane.

 

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How many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case. (d) 2-Bromo-2-methylpentane
 

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How many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case. (c) 3-Bromohexane 
 

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How many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case. (b) 2-Bromohexane.

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How many alkenes would you expect to be formed from each of the following alkyl bromides under conditions of E2 elimination? Identify the alkenes in each case. (a) 1-Bromohexane.
 

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Oxymercuration–demercuration of allyl alcohol gives 1,2-propanediol.

 

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From among the same product choice as Problem 6.68, which one is the major product of the following reaction?

 

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Given that 2-methyl-1-pentene undergoes oxymercuration–demercuration approximately 35 times faster than 2-methyl-2-pentene, predict the major product from oxymercuration– demercuration of limonene.

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Which alkene would be expected to give the following alcohol by oxymercuration– demercuration? 

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 Oxymercuration of methylcyclopentene gives which of the following products?

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The following reaction was performed as part of a research program sponsored by the National Institutes of Health to develop therapeutic agents for the treatment of cocaine addiction. Using what you have seen about the reactions of halogens with alkenes, propose a mechanism for this process. 

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The sex attractant of the female arctiid moth contains, among other components, a compound of molecular formula C21H40  that yields following compound upon ozonolysis. Indetify the structure of sex attractant. 

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A certain compound of molecular formula C19H38 was isolated from fish oil and from plankton. On hydrogenation it gave 2,6,10,14-tetramethylpentadecane. Ozonolysis gave (CH3)2CPO and a 16-carbon aldehyde. What is the structure of the natural product? What is the structure of the aldehyde?  

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The sex attractant by which the female housefl y attracts the male has the molecular formula C23H46 . Catalytic hydrogenation yields an alkane of molecular formula C23H48. Ozonolysis yields 

What is the structure of the housefly sex attractant?    

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Reaction of 3,3-dimethyl-1-butene with hydrogen iodide yields two compounds A and B, each having the molecular formula C6H13I, in the ratio A:B  90:10. Compound A, on being heated with potassium hydroxide in  n-propyl alcohol, gives only 3,3-dimethyl-1-butene. Compound B undergoes elimination under these conditions to give 2,3-dimethyl2-butene as the major product. Suggest structures for compounds A and B, and write a reasonable mechanism for the formation of each.    
 

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(b) On the basis of your answer to part (a), compare the expected stability of 3-methylcyclopropene with that of 1-methylcyclopropene and that of methylenecyclopropane. 

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