Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 15, Problem 15.38P
Interpretation Introduction
Interpretation: The structures of
Concept introduction: Monochlorination is a radical substitution reaction. In this reaction,
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Five isomeric alkanes (A–E) having the molecular formula C6H14 are each treated with Cl2 + hv to give alkyl halides having molecular formulaC6H13Cl. A yields five constitutional isomers. B yields four constitutionalisomers. C yields two constitutional isomers. D yields threeconstitutional isomers, two of which possess stereogenic centers. Eyields three constitutional isomers, only one of which possesses astereogenic center. Identify the structures of A–E.
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Q.) C3H7+
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Draw the product formed when a chlorine atom (Cl)...Ch. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Problem 15.6 Using mechanism 15.1 as guide, write...Ch. 15 - Calculate m0 for the two propagation steps in the...Ch. 15 - Prob. 15.8PCh. 15 - Problem 15.8 Which bond in the each compound is...Ch. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Synthesize each compound from (CH3)3CH. a....Ch. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Draw all constitutional isomers formed when each...Ch. 15 - Draw the structure of the four allylic halides...Ch. 15 - Which compounds can be prepared in good yield by...Ch. 15 - Which CH bond is most readily cleaved in linolenic...Ch. 15 - Prob. 15.23PCh. 15 - Draw the products formed when each alkene is...Ch. 15 - Problem 15.24 When adds to under radical...Ch. 15 - Prob. 15.26PCh. 15 - Draw an energy diagram for the two propagation...Ch. 15 - Prob. 15.28PCh. 15 - Problem 15.27 Draw the steps of the mechanism that...Ch. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Why is a benzylic CH bond labeled in red unusually...Ch. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - What alkane is needed to make each alkyl halide by...Ch. 15 - Which alkyl halides can be prepared in good yield...Ch. 15 - Prob. 15.41PCh. 15 - 15.40 Explain why radical bromination of p-xylene...Ch. 15 - a. What product(s) (excluding stereoisomers) are...Ch. 15 - Prob. 15.44PCh. 15 - Prob. 15.45PCh. 15 - Prob. 15.46PCh. 15 - 15.44 Draw all constitutional isomers formed when...Ch. 15 - Draw the organic products formed in each reaction....Ch. 15 - Prob. 15.49PCh. 15 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 15 - Prob. 15.51PCh. 15 - Prob. 15.52PCh. 15 - Prob. 15.53PCh. 15 - Prob. 15.54PCh. 15 - 15.53 Consider the following bromination: .
a....Ch. 15 - 15.54 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 15.57PCh. 15 - An alternative mechanism for the propagation steps...Ch. 15 - Prob. 15.59PCh. 15 - Prob. 15.60PCh. 15 - Devise a synthesis of each compound from...Ch. 15 - Devise a synthesis of each target compound from...Ch. 15 - Devisea synthesis of each target compound from the...Ch. 15 - Devise a synthesis of each compound using CH3CH3...Ch. 15 - Prob. 15.65PCh. 15 - 15.63 As described in Section 9.16, the...Ch. 15 - 15.64 Ethers are oxidized with to form...Ch. 15 - Prob. 15.68PCh. 15 - Prob. 15.69PCh. 15 - 15.67 In cells, vitamin C exists largely as its...Ch. 15 - What monomer is needed to form each...Ch. 15 - Prob. 15.72PCh. 15 - Prob. 15.73PCh. 15 - 15.71 Draw a stepwise mechanism for the following...Ch. 15 - 15.72 As we will learn in Chapter 30, styrene...Ch. 15 - Prob. 15.76PCh. 15 - 15.74 A and B, isomers of molecular formula , are...Ch. 15 - Prob. 15.78PCh. 15 - Radical chlorination of CH3CH3 forms two minor...Ch. 15 - 15.76 Draw a stepwise mechanism for the...Ch. 15 - Prob. 15.81PCh. 15 - Prob. 15.82PCh. 15 - Prob. 15.83P
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- Consider the following reaction. (a) Draw a structural formula for the compound with the molecular formula C8H12. (b) Do you predict the product to be the cis isomer, the trans isomer, or a mixture of cis and trans isomers? Explain. (c) Draw a suitable stereorepresentation for the more stable chair conformation of the dicarbaldehyde formed in this oxidation.arrow_forwardDetermine the molecular formula based on the information provided.A ketone with M+ = 192 that has4 degrees of unsaturationAn ether with M+ = 154 that has2 degrees of unsaturationarrow_forwardThere are three constitutional isomers with the molecular formula C5H12. Chlorination of one of these isomers yields only one product. Identify the isomer:arrow_forward
- What organic product is formed when 1‑methylcyclopentene is treated with NMMO in the presence of H2O and a catalytic amound of OsO4? Clearly show stereochemistry by drawing a wedge and dashed bond for each chiral carbon. Only draw one stereoisomer if more than one can be formed.arrow_forward3 Name each alkene and specify its configuration by the E,Z system.arrow_forwardDraw the structure of a 1°, 2°, and 3° carbocation, each having molecular formula C4H9+. Rank the three carbocations in order of increasing stability.arrow_forward
- Classify the carbocations as 1º, 2º, or 3º, and rank the carbocations in each group in order of increasing stability.arrow_forwardIdentify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.arrow_forwardWrite the structure of the compound E,E-2,4-Hexadien-1-ol and label each non-equivalent carbon with a letter, A,B,C..arrow_forward
- 2-bromopentane, when treated with alcoholic KOH yields a mixture of three alkenes A, B and C. Identify A, B and C. Which is predominant?arrow_forwardRank the following groups in order of decreasing priority. a. – COOH, – H, – NH2, – OH b. – H, – CH3, – Cl, – CH2CI c. -CH2CH3, -CH3, -H, -CH(CH3)2 d. – CH = CH2, – CH3, – C ≡ CH, – Harrow_forwardHaloalkane with molecular formula, C,H,CI has four structural isomers, A, B, C and D. The structure of A, B and C are shown below. A - (CH3)3CCI B - CH3(CH2)3CI C - CH3CH(CI)CH₂CH3 Give the IUPAC names and classification for isomers A, B and C, respectively. Arrange isomers A, B and C in ascending order of their reactivity with respect to SN1 reaction. Explain your answer. Write the reaction equations involved for the reaction of the most reactive isomer among A, B and C, with respect to SN1 reaction with aqueous KCN, in ethanol under reflux. Show the reaction mechanism. Draw the structure and give IUPAC name of isomer, D. Isomer D reacts with magnesium in anhydrous ether producing an alkyl magnesium chloride E which is then hydrolyzed and produced F, C4H10. Elimination of D with ethanolic KOH under reflux produces G. The treatment of D with sodium metal in ether solvent yields a symmetry alkane H, C8H₁8, which possesses two tertiary carbons. Hydrolysis of D with aqueous sodium…arrow_forward
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