Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 7, Problem 7.46AP
Interpretation Introduction
(a)
Interpretation:
The structure and stereochemistry of the expected products for the addition of
Concept introduction:
Stereochemistry is the study of the arrangement of the atoms and molecules in the space and its effects on the reactions.
The addition reactions on the
Interpretation Introduction
(b)
Interpretation:
The structure and stereochemistry of the expected products for the reaction of cyclopentene with
Concept introduction:
Stereochemistry is the study of the arrangement of the atoms and molecules in the space and its effects on the reactions.
The addition reactions on the alkenes are very common as there is electron density available on the alkene due to double bond electron-cloud.
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Write the structure of the major organic product formed in the reaction of each of the following with hydrogen bromide in the absence of peroxides and in their presence. (a) 1-Pentene (b) 2-Methyl-2-butene (c) 1-Methylcyclohexene
1. Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C8H12.
(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC—(CH2)6—COOH. Draw the structure of W.
(b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethyl sulfide, gives two equivalents of butanedial,
O=CH—CH2CH2—CH=O. Draw the structure of X.
(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation.
(b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active.
(i) Draw TWO (2) possible structures for compound B.
(ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C.
(iii) Name the product formed when compound A undergoes bromination reaction.
Chapter 7 Solutions
Organic Chemistry
Ch. 7 - Prob. 7.1PCh. 7 - Prob. 7.2PCh. 7 - Prob. 7.3PCh. 7 - Prob. 7.4PCh. 7 - Prob. 7.5PCh. 7 - Prob. 7.6PCh. 7 - Prob. 7.7PCh. 7 - Prob. 7.8PCh. 7 - Prob. 7.9PCh. 7 - Prob. 7.10P
Ch. 7 - Prob. 7.11PCh. 7 - Prob. 7.12PCh. 7 - Prob. 7.13PCh. 7 - Prob. 7.14PCh. 7 - Prob. 7.15PCh. 7 - Prob. 7.16PCh. 7 - Prob. 7.17PCh. 7 - Prob. 7.18PCh. 7 - Prob. 7.19PCh. 7 - Prob. 7.20PCh. 7 - Prob. 7.21PCh. 7 - Prob. 7.22PCh. 7 - Prob. 7.23PCh. 7 - Prob. 7.24PCh. 7 - Prob. 7.25PCh. 7 - Prob. 7.26PCh. 7 - Prob. 7.27PCh. 7 - Prob. 7.28PCh. 7 - Prob. 7.29PCh. 7 - Prob. 7.30PCh. 7 - Prob. 7.31PCh. 7 - Prob. 7.32PCh. 7 - Prob. 7.33PCh. 7 - Prob. 7.34APCh. 7 - Prob. 7.35APCh. 7 - Prob. 7.36APCh. 7 - Prob. 7.37APCh. 7 - Prob. 7.38APCh. 7 - Prob. 7.39APCh. 7 - Prob. 7.40APCh. 7 - Prob. 7.41APCh. 7 - Prob. 7.42APCh. 7 - Prob. 7.43APCh. 7 - Prob. 7.44APCh. 7 - Prob. 7.45APCh. 7 - Prob. 7.46APCh. 7 - Prob. 7.47APCh. 7 - Prob. 7.48APCh. 7 - Prob. 7.49APCh. 7 - Prob. 7.50APCh. 7 - Prob. 7.51APCh. 7 - Prob. 7.52APCh. 7 - Prob. 7.53APCh. 7 - Prob. 7.54APCh. 7 - Prob. 7.55APCh. 7 - Prob. 7.56APCh. 7 - Prob. 7.57APCh. 7 - Prob. 7.58APCh. 7 - Prob. 7.59APCh. 7 - Prob. 7.60APCh. 7 - Prob. 7.61APCh. 7 - Prob. 7.62APCh. 7 - Prob. 7.63APCh. 7 - Prob. 7.64APCh. 7 - Prob. 7.65APCh. 7 - Prob. 7.66APCh. 7 - Prob. 7.67APCh. 7 - Prob. 7.68APCh. 7 - Prob. 7.69APCh. 7 - Prob. 7.70APCh. 7 - Prob. 7.71APCh. 7 - Prob. 7.72APCh. 7 - Prob. 7.73APCh. 7 - Prob. 7.74APCh. 7 - Prob. 7.75AP
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- Acid-catalyzed dehydration of 2,2-dimethyl-1-hexanol gave a number of isomeric alkenes including 2-methyl-2-heptene as shown in the following equation.(a) Write a stepwise mechanism for the formation of 2-methyl-2-heptene, using curved arrows to show the flow of electrons. (b) What other alkenes do you think are formed in this reaction?arrow_forward(a) Draw the structure of the following :(i) p-Methylbenzaldehyde (ii) 4-Methylpent-3-en-2-one(b) Give chemical tests to distinguish between the following pairs of compounds :(i) Benzoic acid and Ethyl benzoate, (ii) Benzaldehyde and Acetophenone.(iii) Phenol and Benzoic acid.arrow_forward(1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case? (2) Addition of HBr to 3,3-dimethyl-1-butene gives a mixture of two isomeric alkyl bromide products. Draw structures for the two products, and give a mechanistic explanation for their formation.arrow_forward
- (a) Compound D undergoes a reaction with hydrogen bromide, HBr to produce 2-bromobutane. D exists as cis-trans isomers and decolourises bromine solution in methylene chloride, CH2CI2. (i) Draw and name the structure of compound D. (ii) Draw two (2) constitutional isomers of compound D.arrow_forwardDisiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamylgroups. Disiamylborane is prepared by the reaction of BH3 # THF with an alkene.(a) Draw the structural formulas of the reagents and the products in the preparation ofdisiamylborane.(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why isSia3B not formed?arrow_forward3. (a) Draw the structure of 1-ethylcyclohexene (B). (b) Draw the structures of the two possible products that can result from treating B with hydrogen bromide and very briefly explain which one will be favoured). (c) Draw the curly arrow mechanism for the formation of the favoured productarrow_forward
- trans-3-hexene and cis-3-hexene differ in one of the following ways. Which one? (A) Products of hydrogenation (B) Products of ozonlysis (C) Products of bromine (Br2) addition (D) Products of hydroboration-oxidationarrow_forwardWhich of the following statements about 3-iodo-2-methylprop-1-ene is/are true? (i) It has an E isomer and a Z isomer. (ii) It can be converted to an alkyl lithium compound in one step by reacting with lithium metal. (iii) It would react with the following reagent to give 2-methylhept-1-ene as the product: CuLiarrow_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_forward
- a) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomeric products are formed. Give their structures, and label each asymmetric carbon atom as (R) or (S). What is the relationship between these isomers?arrow_forwardChlorination 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.arrow_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
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