Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Write the reagent or draw structures of the starting material or organic product(s) in
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where possible.
(a)
(b)
HO
OH
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H2SO4
?
Cl₂
?
FeCl3
Give the structure of the product formed when each of the following alkenes reacts with bromine in water: (a) 2-Methyl-1-butene (c) 3-Methyl-1-butene (b) 2-Methyl-2-butene (d) 1-Methylcyclopentene
Chlorination of 2-butanone yields two isomeric products, each having the molecular formula C4H7ClO. (a) What are these two compounds? (b) Write structural formulas for the enol intermediates that lead to each of these compounds. (c) Using curved arrows, show the flow of electrons in the reaction of each of the enols with Cl2.
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 5.1PCh. 5 - Prob. 5.2PCh. 5 - Prob. 5.3PCh. 5 - Prob. 5.4PCh. 5 - Prob. 5.5PCh. 5 - Prob. 5.6PCh. 5 - Prob. 5.7PCh. 5 - Prob. 5.8PCh. 5 - Prob. 5.9PCh. 5 - Prob. 5.10P
Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Prob. 5.13PCh. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - Prob. 5.27APCh. 5 - Prob. 5.28APCh. 5 - Prob. 5.29APCh. 5 - Prob. 5.30APCh. 5 - Prob. 5.31APCh. 5 - Prob. 5.32APCh. 5 - Prob. 5.33APCh. 5 - Prob. 5.34APCh. 5 - Prob. 5.35APCh. 5 - Prob. 5.36APCh. 5 - Prob. 5.37APCh. 5 - Prob. 5.38APCh. 5 - Prob. 5.39APCh. 5 - Prob. 5.40APCh. 5 - Prob. 5.41APCh. 5 - Prob. 5.42APCh. 5 - Prob. 5.43APCh. 5 - Prob. 5.44APCh. 5 - Prob. 5.45APCh. 5 - Prob. 5.46APCh. 5 - Prob. 5.47APCh. 5 - Prob. 5.48APCh. 5 - Prob. 5.49APCh. 5 - Prob. 5.50APCh. 5 - Prob. 5.51APCh. 5 - Prob. 5.52APCh. 5 - Prob. 5.53APCh. 5 - Prob. 5.54AP
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Write the structure of the major organic product obtained by hydroboration–oxidation of each of the following alkenes: (a) 2-Methylpropene (d) Cyclopentene (b) cis-2-Butene (e) 3-Ethyl-2-pentenearrow_forwardPhotochemical chlorination of 2,2,4-trimethylpentane gives four isomeric monochlorides. (a) Write structural formulas for these four isomers. (b) The two primary chlorides make up 65% of the monochloride fraction. Assuming that all the primary hydrogens in 2,2,4-trimethylpentane are equally reactive, estimate the percentage of each of the two primary chlorides in the product mixture.arrow_forwardName and draw a structural formula for the major product of each alkene addition reaction: CH S (a) CH₂C=CH₂ + HI →→→→ (b) CH 3 + HClarrow_forward
- Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents. (a) concentrated HBr (b) TsCl/pyridine, then NaBrarrow_forwardGive the product(s) formed when 1-butene reacts with the following: (a) HBr (b) dilute H2SO4 (c) Br2 in CCl4 (d) Br2 in H2Oarrow_forward3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) dimethyl sulfoxide (DMSO) is used in place of methanol (b) methanol is used by itself without sodium methoxide (c) 1-chloro-2,2,-dimethylpropane is used in place of 3-chloro-2-methylpropenearrow_forward
- Draw structural formulas for these compounds. (a) 1-Bromo-2-chloro-4-ethylbenzene (b) 4-Bromo-1,2-dimethylbenzene (c) 2,4,6-Trinitrotoluene (d) 4-Phenyl-1-pentene (e) p-Cresol (f) 2,4-Dichlorophenolarrow_forward6) Which is the organic product for the following reaction? (a) (b) (c) (d) LOH OH COOH OH OH COOH COOH KMnO4 H₂O (e) None of the above products will be formedarrow_forwardand (ii) KMnO4 in aqueous NaOH: 1. Name the following alkenes, and predict the products of their reaction with (i) KMnO4 in aqueous acid (a) (b) 2. Draw structures corresponding to the following IUPAC names: (a) 3-Ethylhept-1-yne (b) 3,5-Dimethylhex-4-en-1-yne (c) Hepta-1,5-diyne (d) 1-Methylcyclopenta-1,3-diene (1) 3. Draw and name all the possible pentyne isomers, C5H8. H H Ç-H [ Pent-1-yne] (2) 4. Predict the products of the following ring is inert to all the indicated reagents.) 4 H 4- (3) 4-C C = C-4 [3-methylbut -1-4 [Pent-2-yhdioselectivity where relevant. (The aromatic CH=CH2 Styrene (a) Styrene+H2 Pd, ? (c) Styrene+HBr ? (b) Styrene+Br2 → ? (d) Styrene+KMnO4 NaOH, H2O ? 5. Suggest structures for alkenes that give the following reaction products. There may be more than one answer for some cases. HyPd catalyst (a) ? Br₂ in CH2Cl2 (b) ? HBr (c) ? 2-Methylhexane 2,3-Dibromo-5-methylhexane 2-Bromo-3-methylheptane CH3 HO OH CH3CHCH2CHCHCH2CH3 KMnO4OH (d) ? H₂Oarrow_forward
- Compounds B and C are hydrocarbons with the structural formulae as shown below. CH, „CH, в (a) Name compounds B and C according to the IUPAC nomenclature. (b) Both B and C can undergo oxidation reaction with the same oxidizing agent. Write chemical equations involved and explain the differences between these two reactions. (c) Name one reaction that converts B to methylcyclohexane.arrow_forwardBiphenyl has the following structure.(a) Is biphenyl a (fused) polynuclear aromatic hydrocarbon?(b) How many pi electrons are there in the two aromatic rings of biphenyl? How does this number compare with that for naphthalene?(c) The heat of hydrogenation for biphenyl is about 418 kJ>mol (100 kcal>mol). Calculate theresonance energy of biphenyl.(d) Compare the resonance energy of biphenyl with that of naphthalene and with that of two benzene rings. Explain thedifference in the resonance energies of naphthalene and biphenyl.arrow_forwardprovide the structure of the intermediate and product for the following reaction : (c) H CH,OH/H (C)arrow_forward
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