Lab Report 2

Compounds A and B are isomers having molecular formula C5H12. Heating A with Cl2 gives a single product of monohalogenation, whereas heating B under the same conditions forms three constitutional isomers. What are thestructures of A and B?

Gg.211.

Na, NH3 H3C-C=C-CH3 CH3 H3C° Alkynes are reduced to trans alkenes by a process called dissolving metal reduction. The reaction uses sodium or lithium metal as the reducing agent and liquid ammonia as the solvent. The method is specific in the formation of trans alkenes from alkynes. The method involves two successive transfers of single electrons from the alkali metal to the triple bond, with abstraction of protons from the ammonia solvent. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions .CH3 H-NH2 CH3 :NH2 H3C H3C

2. Spiropentane has unusual strain and hybridization. The structure of spiropentane has been determined by X-ray crystallography. The endocyclic angles at the spiro carbon are about 62°, and the bond angles between C-C bonds in the adjacent rings are about 137°. How would you relate the strain to the hybridization of each carbon in spirocyclopentane based on these bond angles? 62° 137⁰ spiropentane

1,3-Cyclohexadiene and 1,4-cyclohexadiene can be distinguished by reaction with ozone and then treatment with zinc.  Draw the structures of the products produced by ozonolysis of the two compounds.

7.33 a-Farnesene is a constituent of the natural wax found on apples. What is its IUPAC name, including stereochemistry? 7.34 Menthene, a hydrocarbon found in mint plants, has the systematic name 1-isopropyl-4-methylcyclohexene. Draw its structure. 7.35 Draw and name the six alkene isomers, C5H1o, including E,Z isomers. a-Famesene 8.22 Name the following alkenes, and predict the products of their reaction with (1) meta-chloroperoxybenzoic acid, (2) KMnO4 in aqueous acid, and (3) 03, followed by Zn in acetic acid: (a) (b) (a) 8.23 Draw the structures of alkenes that would yield the following alcohols on hydration (red = O). Tell in each case whether you would use hydroboration- oxidation or oxymercuration-demercuration. (b)

C10T05Q3420 Give the major organic product for the following reaction. H H H catalytic heat if There is no reaction under these conditions or the correct product is not listed here.

Isotretinoin is a retinoid derivative of vitamin A used in the treatment of severe recalcitrant acne. What is the degree of substitution of the encircled alkene functional group in its structure? HO, A trisubstituted monosubstituted tetrasubstituted D disubstituted

Draw the structure of each product from the reaction of benzene with 2-chloro-1-methylcyclohexane using AlCl 3 as the catalyst and Identify the major product.

One compound that contributes to the “seashore smell” at beaches in Hawai‘i is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'?

∆H° values obtained for a series of similar reactions are one set of experimental data used to determine the relative stability of alkenes. Explain how the following data suggest that cis-but-2-ene is more stable than but-1-ene (Section 12.3A).

What is the name of the following molecule Ph-CH2-CH2-CH2-CH=CH2? * styrene 5-phenyl-1-PENTENE 1-phenyl-4-PENTENE 3-benzyl-1-BUTENE allylbenzene

Compound W has molecular formula C₁4H18 and reacts with H₂ to form X. Oxidative cleavage of W with O3 followed by CH3 SCH3 affords Y. What is the structure of W?

A 2-bromobutane react with methanol and form a enantiomeric pair of 2-methoxybutane. Draw the structures of the enntiomeric pairs of ethers.

Compound A and compound B are constitutional isomers with molecular formula C3H,CI. Treatment of compound A with sodium methoxide (NaOMe), a substitution reaction predominates. When compound B is treated with sodium methoxide, an elimination reaction predominates. Propose structures for compounds A and B. compound A: Draw Your Solution eTextbook and Media: compound 8: Draw Your Solution

CCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*

Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.