Concept explainers
Interpretation:
Given that myrcene is isomeric with β-ocimene with molecular formula C10H16 has UV absorption maxima 226 nm. On catalytic hydrogenation it gives 2,6-dimethyloctane. Upon ozonolysis followed by treatment with Zn and acetic acid it gives formaldehyde, acetone and 2-oxopentanediol. The structure for myrcene is to be proposed and the reactions are to be given showing the starting materials and products.
Concept introduction:
The UV absorption at 226 nm indicates a conjugated system. The
To propose:
Based on the data the structure for myrcene and to give the reactions showing the starting materials and products.
Want to see the full answer?
Check out a sample textbook solutionChapter 14 Solutions
Organic Chemistry
- alkylation of benzene with 1-chlorobutane in the presence of AlCl3 gives both butylbenzene and (1-methylpropyl)benzene as products. Propose a route to butylbenzene from benzene that does not also give the (1-methylpropyl)benzene side-product.arrow_forwardA certain hydrocarbon, C5H6, yields the two products shown below upon ozonolysis with 1. O3/CH2Cl2 2. Zn/H3O . Deduce the structure of the hydrocarbon.arrow_forwardShow the stereochemistry of the epoxide (see Problem 11-31) you would obtain by formation of a bromohydrin from trans-2-butene, followed by treatment with base.arrow_forward
- (g) butan-2-one, CH3CH2COCH39-37 Show how you would synthesize the following compounds, starting with acetylene and any compounds containing nomore than four carbon atoms. 2,2-dibromohexanearrow_forward(2E,4Z,6Z,8E)-decatetraene has been cyclized to give 7,8-dimethy-1,3,5-cyclooctatriene. Predict the manner of ring-closure conrotatory or disrotatory for both thermal and photochemical reactions, and predict the stereochemistry of product in each case. Show how to get the answerarrow_forwardAs an example of a ver rare occurence, the following hydrocarbon reacts with two equivalents of butylithium to form a dianion of the formula [C8H6]2- . Propose a structure for this dianion and explain why this dianion forms so readily.arrow_forward
- Hydration of 2-pentyne gives a mixture of two ketones, each with the molecular formula C5H10O. Propose structural formulas for these two ketones and for the enol from which each is derivedarrow_forwardSuggest a strategy for converting 1-methylcyclohexene into 1-cyclohexylmethanol. Provide the structures for the major organic products frormed in each step.arrow_forwardThe aryl diene undergoes sequential Heck reactions to give a product with the molecular formula C15H18. Propose a structural formula for this product.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningGeneral, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
- Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,