Concept explainers
Interpretation:
The structure of each alkene is to be drawn and classified on the basis of substitution on the double bond, the structure of product formed from each alkene on hydrogenation is to be written, the heat of hydrogenation can be used to relate the relative stabilities of
Concept introduction:
Hydrogenation of alkenes or
Stability of the isomers is inversely proportional to the steric hindrance. The more the steric hindrance, the lesser will be the stability of isomer.
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Chapter 7 Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
- Arrange the alkenes in each set in order of increasing rate of reaction with HI and explain the basis for your ranking. Draw the structural formula of the major product formed in each case. (a) and (b) H3CH₂CHC=CH₂ and (H3C) 2C=CHCH3arrow_forward(d) When butane, CH3CH2CH2CH3 and bromine gas, Br2 is exposed to sunlight, monobrominated product are produced. The reaction equation is given below: uv CH;CH,CH,CH3 + Br2 A + B (i) State the type of reaction. (ii) What is the function of the sunlight in the reaction? (iii) Draw the structure of monosubstituted products, A and B. Label the major product. (iv) Draw the propagation steps in the mechanism for the formation of the major product.arrow_forward1)Chemistry students are taking an experimental course in organic chemistry at a public university. During an experiment involving conjugated dienes, some doubts arose when discussing the results obtained so far: (a) A student obtained two products from the reaction of 1,3-cyclohexadiene with Br2. His lab partner was surprised to get only one product from the reaction of 1,3 - cyclohexadiene with HBr. Explain these distinct results. (b) One student, seeing the discussion of colleagues, commented that she obtained two distinct products when reacting 1,3,5-hexatriene with HBr, with different yields just by changing the reaction temperature. Explain the results she obtained using reaction mechanism and based on kinetic and thermodynamic control involving conjugated dienes.arrow_forward
- Compound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the structure of compound Z. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Ignore alkene stereochemistry. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodlearrow_forwardGive reasons: (i) C—Cl bond length in chlorobenzene is shorter than C—Cl bond length in CH3—Cl.(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(iii) SN1 reactions are accompanied by racemization in optically active alkyl halidesarrow_forwardAssign E or Z stereochemistry to each of the following alkenes, and convert each drawing into a skeletal structure (red = 0, yellow-green = Cl). (a) (b)arrow_forward
- Consider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)arrow_forward(c) A series of dialkyl ethers react with excess hydrogen bromide, with the following results. Analyze the ether in each case and write out the complete chemical equations. (1) Ether gives a mixture of bromocyclopentane and 1-bromoethane. (ii) Another ether gives one mole of 1,5-dibromopentane per mole of ether.arrow_forward2.arrow_forward
- (a) Give the names of reagents and conditions for each of the reactions I and IIarrow_forward(a) Account for the following :(i) Electrophilic substitution reactions in haloarenes occur slowly.(ii) Haloalkanes, though polar, are insoluble in water.(b) Arrange the following compounds in increasing order of reactivity towards SN2 displacement:2-Bromo-2-Methylbutane, 1-Bromopentane, 2-Bromopentanearrow_forward7.1 Provide the line structures of the products formed in the following reactions. One block may represent more than one product. (a) HBr Diethyl ether (b) H,0, H*arrow_forward