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
- The German chemist Wilhelm Kӧrner (1839-1925) observed in 1974 that each of the three isomers of dibromobenzene, A, B, and C, gave a different number of tribromobenzenes upon further bromination, allowing him to assign their respective structures. Try to do the same and assign structures to A, B, and C based on the following results: A gives two tribromobenzenes in comparable amounts B gives three tribromobenzenes, one of them in minor quantities C gives only one tribromobenzenearrow_forwardGive the series of reactions below, identify and give the iupac name for the following compounds, in short identify and name A,B,Carrow_forwardOn being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) yielded a mixture of two alkenes B and C, each having the molecular formula C7H14. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3-ethylpentane. Suggest structures for compounds A, B, and C consistent with these observations.arrow_forward
- Compound A has molecular formula C4H10, and gives two monochlorides, B and C, on photochemical chlorination. Treatment of either of these monochlorides with potassium tert-butoxide gives the same alkene (C4H8) as the product, but B leads to just one isomer of the alkene, D, where C gives D and another isomer of the alkene, E. Treatment of monochlorides B and C with aqueous ethanol gives products F and G, respectively, both of which are of molecular formula C4H10O. What are the names of compounds A-G?arrow_forwardWhat is the molecular model for cis-1,3-dichlorocyclohexane and discuss its most stable conformation and the 1,3-diaxial interaction.arrow_forwardProvide a mechanism which explains the following conversions. Include all intermediates (where appropriate) and watch your arrows and chargesarrow_forward
- In the following three compounds(1,2,3) arrange their relative reactivity towards the reagent CH3Cl / AlCl3. and justify it.arrow_forwardCompound A(C10H12O)gives off oxygen on treatment with sodium metal and also decolorizes Br2 in CCl4 to give organic compound B. Compound A on treatment with I2 in NaOH gives iodoform and salt C which after acidification gives a white solid D(C7H6O2). Using knowledge of organic chemistry identify structures A,B,C and Darrow_forwardThe reaction of 3,4-dimethyl-3-hexanol (3,4-dimethylhexan-3-ol) with HBr generates compound A as the major product. Treatment of compound A with a strong base gives two isomers of compound B as the major product, along with one isomer of compound C and one isomer of compound D as minor products, all of which have one double-bond equivalent. Identify compounds A, B, C, and D and give their names. By what mechanism does the reaction of 3,4-dimethyl-3-hexanol with HBr occur? By what mechanism does the reaction of A with strong base to form B occur? Propose reaction conditions for an alternative, one-step method for converting 3,4-dimethyl-3-hexanol directly to compound B.arrow_forward
- Provide a mechanism which explains the following conversions. Include all intermediates and watch you arrows and chargesarrow_forwardγ-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since γ-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. γ-Butyrolactone shows an absorption in its IR spectrum at 1770 cm−1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of γ-butyrolactone?arrow_forwardA difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. c. Suggest a reagent to convert A to the single stereoisomer X.arrow_forward