Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 18, Problem 18.48P
Consider the tetracyclic
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(a) Draw two different enol tautomers of 2-methylcyclohexanone. (b) Draw two constitutional
isomers that are not tautomers, but contain a C=C and an OH group.
2-methylcyclohexanone
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(a) Draw the products (including stereoisomers) formed when 2methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.
Chapter 18 Solutions
Organic Chemistry
Ch. 18 - Prob. 18.1PCh. 18 - Prob. 18.2PCh. 18 - Prob. 18.3PCh. 18 - Prob. 18.4PCh. 18 - Prob. 18.5PCh. 18 - Prob. 18.6PCh. 18 - Prob. 18.7PCh. 18 - Prob. 18.8PCh. 18 - Problem 18.9 Draw the product of each reaction
a....Ch. 18 - Prob. 18.10P
Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Prob. 18.13PCh. 18 - Problem 18.14 Draw all resonance structures for...Ch. 18 - Problem 18.15 Classify each substituent as...Ch. 18 - Prob. 18.16PCh. 18 - Problem 18.17 Label each compound as more or less...Ch. 18 - Problem 18.18 Rank the following compounds in...Ch. 18 - Prob. 18.19PCh. 18 - Problem 18.20 Draw the products of each...Ch. 18 - Prob. 18.21PCh. 18 - Problem 18.22 Draw the products formed when each...Ch. 18 - Problem 18.23 Devise a synthesis of each compound...Ch. 18 - Problem 18.24 Draw the products of each...Ch. 18 - Problem 18.25 Draw a stepwise mechanism for the...Ch. 18 - Problem 18.26 Draw the products of each...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Problem 18.29 How could you use ethylbenzene to...Ch. 18 - Prob. 18.30PCh. 18 - Problem 18.31 What steps are needed to convert...Ch. 18 - Problem 18.32 Synthesize each compound from...Ch. 18 - Problem 18.33 Synthesize each compound from...Ch. 18 - Prob. 18.34PCh. 18 - 18.35 What is the major product formed by an...Ch. 18 - 18.36 Draw the products formed when phenol is...Ch. 18 - Problem 18.37 Draw the products formed when each...Ch. 18 - 18.38 Draw the products of each reaction.
a. d....Ch. 18 - 18.39 What products are formed when benzene is...Ch. 18 - 18.40 Draw the products of each reaction.
c.
d....Ch. 18 - 18.41 You have learned two ways to make an alkyl...Ch. 18 - 18.42 Draw the structure of A, an intermediate in...Ch. 18 - Prob. 18.43PCh. 18 - Prob. 18.44PCh. 18 - 18.45 Explain why each of the following reactions...Ch. 18 - Prob. 18.46PCh. 18 - 18.47 For each of the following substituted...Ch. 18 - 18.48 Consider the tetracyclic aromatic compound...Ch. 18 - 18.49 For each N-substituted benzene, predict...Ch. 18 - Prob. 18.50PCh. 18 - 18.51 Using resonance structures, explain why a...Ch. 18 - Prob. 18.52PCh. 18 - 18.53 Rank the aryl halides in each group in order...Ch. 18 - 18.54 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.55PCh. 18 - 18.56 Draw a stepwise, detailed mechanism for the...Ch. 18 - Prob. 18.57PCh. 18 - 18.58 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - 18.63 Synthesize each compound from benzene and...Ch. 18 - Problem 18.64 Synthesize each compound from...Ch. 18 - Prob. 18.65PCh. 18 - Prob. 18.66PCh. 18 - Prob. 18.67PCh. 18 - Prob. 18.68PCh. 18 - Problem 18.69 Identify the structures of isomers A...Ch. 18 - Prob. 18.70PCh. 18 - Problem 18.71 Compound X (molecular formula ) was...Ch. 18 - 18.72 Reaction of p-cresol with two equivalents of...Ch. 18 - Prob. 18.73PCh. 18 - The NMR spectrum of phenol () shows three...Ch. 18 - Explain the reactivity and orientation effects...Ch. 18 - Prob. 18.76PCh. 18 - Prob. 18.77PCh. 18 - Prob. 18.78PCh. 18 - Prob. 18.79P
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- For alkenes A, B, C, and D: (a) Rank A—D in order of increasing heat of hydrogenation; (b) rank A—D in order of increasing rate of reaction with H2, Pd-C; (c) draw the products formed when each alkene is treated with ozone, followed by Zn, H2O.arrow_forward(a) Give an acceptable name for compound A. (b) Draw the organic products formed when A is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.arrow_forwardFor alkenes A, B, and C: (a) Rank A, B, and C in order of increasing heat of hydrogenation; (b) rank A, B, and C in order of increasing rate of reaction with H2, Pd-C; (c) draw the products formed when each alkene is treated with ozone, followed by Zn, H2O.arrow_forward
- The ether, CH3OCH2CH3, can be prepared by two different nucleophilic substitution reactions, one using CH3O- as nucleophile and the other using CH3CH2O- as nucleophile. Draw both routes.arrow_forward(a) Draw the structure of the hemiacetal formed from one mole of benzaldehyde and one mole of ethanol. (b) Draw the structure of the acetal formed from one mole of benzaldehyde and two moles of ethanol. (c) Draw the structure of 2-methoxy-2-butanol. What compounds could you prepare this from? (d) Draw the structure of 3-methoxyl-2-butanol. What functional groups are present? Is this an acetal, a hemiacetal, or neither? Explain. (e) Identify the functional groups in the molecules shown below. Circle any acetals or hemiacetal, and identify which they are. 0-arrow_forwardPQ-2. This reaction is classified as (A) a nucleophilic addition. (C) a nucleophilic substitution. NaCN H3C CH3 H₂O (B) an electrophilic addition. (D) an electrophilic substitution. HO H3C CN CH3arrow_forward
- (a) Give an acceptable name for each compound, (b) Draw the organic products formed when A or B is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.arrow_forwardThe bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown. (a) Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole. (b) Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline. (c) Explain whyelectrophilic substitution occurs more readily at C3 rather than C2 of indole.arrow_forwardA is a toxin produced by the poisonous seaweed Chlorodesmis fastigiata. (a) Label each alkene that exhibits stereoisomerism as E or Z. (b) Draw a stereoisomer of A that has all Z double bonds.arrow_forward
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