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Concept explainers
(a)
Interpretation:
Without consulting tables or figures, answer the following questions: a thermal disrotatory electrocyclic reaction involving 12 electrons allowed or forbidden-the statement is to be verified.
Concept introduction:
Electrocyclic reactions are a pericyclic reaction which occur intramolecularly. These reactions will result in the formation of ring compounds under the influence of heat or light. Notably, in this process one new sigma bond is formed and one old π-bond is consumed. Intriguingly, the reverse ring opening electrocyclic reaction can also be possible to occur under the same reaction mechanism but in reverse manner. According to molecular orbital concepts, systems having 4n π electrons undergoes conrotatory ring closure is allowed and this ring closure is forbidden for systems having 4n + 2 π systems. Similarly, disrotatory closing of rings is forbidden for 4n π electrons and allowed for 4n + 2 π electron systems.
(b)
Interpretation:
a [8s + 4s] photochemical cycloaddition is allowed-the statement is to be verified.
Concept introduction:
The reactions in which the formation of cyclic product observed by combining two or more unsaturated molecules is called cyclo addition reaction. Besides, the net reduction of bond multiplicity is observed. Molecules having 4n π electrons is allowed under photochemical conditions and 4n +2 π electrons is allowed under thermal conditions.
(c)
Interpretation:
the HOMO of (Z)-3, 4-dimethyl-1, 3, 5-hexatriene symmetric or antisymmetric-the statement is to be verified.
Concept introduction:
The reactions in which the formation of cyclic product observed by combining two or more unsaturated molecules is called cyclo addition reaction. Besides, the net reduction of bond multiplicity is observed. Molecules having 4n π electrons is allowed under photochemical conditions and 4n +2 π electrons is allowed under thermal conditions.
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Chapter 28 Solutions
EBK ORGANIC CHEMISTRY
- Is it option (b)1-bromo-6-chlorocyclohexene?arrow_forward(3) HI does not undergo free radical addition with 1-butene, even in the presence of a peroxide. Please provide an explanation by analyzing the propagation steps if the same radical reaction occurred with HI. Besides the bond dissociation enthalpies in the appendix, the following approximate bond dissociate enthalpies might be useful to you: ~310 kJ/mol The component of C=C CH3CH₂CH₂CH₂-Br CH3CH₂CH₂CH2-I -290 kJ/mol (C-Br bond) ~235 kJ/mol (C-I bond)arrow_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_forward
- Give to all parts? (a) Give the complete mechanism for the reaction of trans-2-butene with Br2 in excess H2O. (b) Name the products (including stereochemistry). (c) Give the complete mechanism for the reaction of trans-2-butene with Br2 in excess H2O. (d) Name the products (including stereochemistry).arrow_forwardUsing one or more of the following compounds as starting materials or products illustrate, with an example, each of the following type of pericyclic reactions. Your answer should include curved arrow mechanisms. (i) a disrotatory thermal electrocyclic reaction (ii) a conrotatory photochemical electrocyclic reaction (iii) a [4+2] cycloaddition (iv) a [3,3]-sigmatropic rearrangementarrow_forward2. Provide the final product for each of the following reactions: a) 1-methylcyclohexene reacts with H,O/H,SO, b) Vinylcyclopentane reacts with (a) BH, THF and (b) OH, H,0, H,0 c) 1-chlorohexane reacts with hydroxide ionarrow_forward
- Classify the following dienes and polyenes as isolated, conjugated, cumulated, or some combination of theseclassifications.(a) cycloocta-1,4-diene (b) cycloocta-1,3-diene (c) cyclodeca-1,2-diene(d) cycloocta-1,3,5,7-tetraene (e) cyclohexa-1,3,5-triene (benzene) (f) penta-1,2,4-trienearrow_forwardPredict the major products of the following reactions, including stereochemistry.(a) cyclohexene + KMnO4>H2O (cold, dilute)(b) cyclohexene + peroxyacetic acid in waterarrow_forwardConsider 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. -SH C NaOH Draw only the organic product. Select /// Draw Rings More C H S Erase:arrow_forward
- Draw a structure for each compound (includes old and new names).(a) 3-methylpent-1-ene (b) cis-3-methyl-3-hexene (c) 3,4-dibromobut-1-ene(d) 1,3-cyclohexadiene (e) cycloocta-1,4-diene (f) (Z)-3-methyl-2-octene(g) vinylcyclopropane (h) (Z)-2-bromo-2-pentene (i) (3Z,6E)-1,3,6-octatrienearrow_forward4.35 Formulate the reaction of cyclohexene with (i) Br2 and (ii) meta-chloro- peroxybenzoic acid followed by H30+. Show the reaction intermediates and the final products with correct cis or trans stereochemistry. 4.36 What products would you expect to obtain from reaction of cyclohexa- 1,3-diene with each of the following? (a) 1 mol Br2 in CH2C12 (c) 1 mol DCl (D = deuterium, ²H) (b) 1 mol HCl (d) 2 mol H2 over a Pd catalyst 4.37 Predict the products of the following reactions on hex-1-yne: (a) 1 equiv HBr ? (b) 1 equiv Cl2 ? (c) H2, Lindlar catalystarrow_forwardDraw a structure for each compound (includes old and new names).(a) 3-methylpent-1-ene (b) cis-3-methyl-3-hexene (c) 3,4-dibromobut-1-ene(d) 1,3-cyclohexadiene (e) cycloocta-1,4-diene (f) (Z)-3-methyl-2-octene(g) vinylcyclopropanearrow_forward
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