Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 24.SE, Problem 60AP
Interpretation Introduction
a) Br2 (1 equivalent)
Interpretation:
To draw the structure of the organic products from the reaction of m-toulidine toluidine (m-methylaniline) with the following reagents.
Interpretation Introduction
b) CH3I (excess)
Interpretation:
To draw the structure of the organic products from the reaction of m-toulidine toluidine (m-methylaniline) with the following reagents.
Interpretation Introduction
c) CH3COCl in pyridine
Interpretation:
To draw the structure of the organic products from the reaction of m-toulidine toluidine (m-methylaniline) with the following reagents.
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(a) Write the structures of main products when aniline reacts with the following reagents :(i) Br2 water (ii) HCI (iii) (CH3CO)2O/pyridine(b) Arrange the following in the increasing order of their boiling point :C2H5NH2, C2H5OH, (CH3)3N(c) Give a simple chemical test to distinguish between the following pair of compounds : (CH3)2NH and (CH3)3N
(a) Write the chemical reaction involved in Wolff-Kishner reduction.(b) Arrange the following in the increasing order of their reactivity towards nucleophilic addition reaction:C6H5COCH3, CH3— CHO, CH3COCH3(c) Why carboxylic acid does not give reactions of carbonyl group?
1. (a) Oxidation of 1-butanol with PCC will produce which of the following?
2-chlorobutanal
butanone
butanoic acid
butanal
(b) Which synthetic route is the best way to prepare ethyl isopropyl ether?
CH3CH2OH + (CH3)2CHOH + H2SO4, 140 oC
CH3CH2ONa + (CH3)2CHOH
CH3CH2ONa + (CH3)2CHBr
(CH3)2CHONa + CH3CH2Br
(c) The Williamson ether synthesis involves nucleophilic substitution involving an alkyl halide and an alcohol. (True or False)
Chapter 24 Solutions
Organic Chemistry
Ch. 24.1 - Name the following compounds:Ch. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.3 - Prob. 4PCh. 24.3 - The benzylammonium ion (C6H5CH2NH3+) has pKa =...Ch. 24.4 - Prob. 6PCh. 24.5 - Prob. 7PCh. 24.6 - Prob. 8PCh. 24.6 - Prob. 9PCh. 24.6 - Show two methods for the synthesis of dopamine, a...
Ch. 24.6 - Prob. 11PCh. 24.6 - Prob. 12PCh. 24.6 - Prob. 13PCh. 24.7 - Prob. 14PCh. 24.7 - Prob. 15PCh. 24.8 - Prob. 16PCh. 24.8 - Propose syntheses of the following compounds from...Ch. 24.8 - How would you prepare the following compounds from...Ch. 24.8 - Prob. 19PCh. 24.9 - Draw an orbital picture of thiazole. Assume that...Ch. 24.9 - Prob. 21PCh. 24.9 - Prob. 22PCh. 24.9 - Which nitrogen atom in the hallucinogenic indole...Ch. 24.9 - Prob. 24PCh. 24.10 - Prob. 25PCh. 24.SE - Name the following amines, and identify each as...Ch. 24.SE - The following compound contains three nitrogen...Ch. 24.SE - Name the following amine, including R, S...Ch. 24.SE - Prob. 29VCCh. 24.SE - Predict the product(s) for each reaction below and...Ch. 24.SE - Predict the product(s) and provide the complete...Ch. 24.SE - Prob. 32MPCh. 24.SE - Predict the product(s) and provide the mechanism...Ch. 24.SE - The diazotization of aniline first involves the...Ch. 24.SE - Prob. 35MPCh. 24.SE - Prob. 36MPCh. 24.SE - Prob. 37MPCh. 24.SE - Prob. 38MPCh. 24.SE - Choline, a component of the phospholipids in cell...Ch. 24.SE - Prob. 40MPCh. 24.SE - -Amino acids can be prepared by the Strecker...Ch. 24.SE - Prob. 42MPCh. 24.SE - Prob. 43MPCh. 24.SE - Prob. 44MPCh. 24.SE - Propose a mechanism for the following reaction:Ch. 24.SE - Prob. 46MPCh. 24.SE - Name the following compounds:Ch. 24.SE - Prob. 48APCh. 24.SE - Prob. 49APCh. 24.SE - Prob. 50APCh. 24.SE - Histamine, whose release in the body triggers...Ch. 24.SE - Prob. 52APCh. 24.SE - Prob. 53APCh. 24.SE - Prob. 54APCh. 24.SE - Prob. 55APCh. 24.SE - Prob. 56APCh. 24.SE - Prob. 57APCh. 24.SE - Prob. 58APCh. 24.SE - Prob. 59APCh. 24.SE - Prob. 60APCh. 24.SE - Show the products from reaction of p-bromoaniline...Ch. 24.SE - Prob. 62APCh. 24.SE - How would you prepare the following compounds from...Ch. 24.SE - Prob. 64APCh. 24.SE - Phenacetin, a substance formerly used in...Ch. 24.SE - Prob. 66APCh. 24.SE - Draw the structure of the amine that produced the...Ch. 24.SE - Fill in the missing reagents a-e in the following...Ch. 24.SE - Prob. 69APCh. 24.SE - Prob. 70APCh. 24.SE - Deduce the structure of the compound with formula...Ch. 24.SE - Prob. 72APCh. 24.SE - Prob. 73APCh. 24.SE - Prob. 74APCh. 24.SE - Prob. 75APCh. 24.SE - Prob. 76APCh. 24.SE - Propose a structure for the product with formula...Ch. 24.SE - Prob. 78APCh. 24.SE - Prob. 79APCh. 24.SE - Prob. 80APCh. 24.SE - Prob. 81APCh. 24.SE - Prob. 82APCh. 24.SE - Prob. 83APCh. 24.SE - Prob. 84AP
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- 1. (a) Oxidation of 1-butanol with PCC will produce which of the following? 2-chlorobutanal butanone butanoic acid butanal (b) Which synthetic route is the best way to prepare ethyl isopropyl ether? CH3CH2OH + (CH3)2CHOH + H2SO4, 140 oC CH3CH2ONa + (CH3)2CHOH CH3CH2ONa + (CH3)2CHBr (CH3)2CHONa + CH3CH2Brarrow_forwardn-Pentanol (CH3CH2CH2CH2CH2OH) and 2-methylbutan-2-ol (CH3CH2C(CH3)2OH) are converted to their corresponding alkyl chorides on being reacted with hydrogen chloride. (a) Write out an equation for each reaction (b) Assign each the appropriate symbol (SN1 or SN2) (c) Write a suitable mechanism for each reactionarrow_forward3. (a) Based on the following reaction scheme, answer the following questions: CH;č - OCH,CH3 CH;C-OH Compound W Compound D H2O, H* SOCI, heat Compound Z Compound X + Compound Y (i) Give the structural formula of compounds X, Y and Z.arrow_forward
- Hydride reduction (with LiAlH4 or NaBH4) of each of the following ketones has been reported in the chemical literature and gives a mixture of two diastereomeric alcohols in each case. Give the structures of both alcohol products for each ketone.(a) (S)-3-Phenyl-2-butanone(b) 4-tert-Butylcyclohexanonearrow_forwardGive reasons :(a) n-Butyl bromide has higher boiling point than f-butyl bromide.(b) Racemic mixture is optically inactive.(c) The presence of nitro group (-NO2) at o/p positions increases the reactivity of haloarenes towards nucleophilic substitution reactions.arrow_forwardConsider the following structural formulas. OH H;C CH3 CH3 F G H (a) Which of the compounds F-l can easily be subjected to an elimination reaction? (b) Provide the reaction mechanism for all eliminations under (a).arrow_forward
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- (a) Aniline is oxidized and then resulting product is boiled with Conc. HNO3 and conc. H2S04. (b) Cyclopentylnitrile is reduced with LIAIH4 and the resulting product reacts with benzenesulphonylchloride (c) 2-Chloro-5-methyl-diethylhexandioate is condensed in alkaline medium (d) 2-Methylethylpropanoate is condensed with phenylbenzanoate in an alkaline medium (e) When Ethanoic is heated with NH3 and resulting product reacts with benzoylchloride.arrow_forwardWrite the structure of the principal organic product formed in the reaction of 1-propanol with each of the following reagents:(a) Sulfuric acid (catalytic amount), heat at 140°C(b) Sulfuric acid (catalytic amount), heat at 200°C(c) Dimethyl sulfoxide (DMSO), oxalyl chloride [(COCl)2], triethylamine [N(CH2CH3)3](d) Pyridinium chlorochromate (PCC) in dichloromethane(e) Potassium dichromate (K2Cr2O7) in aqueous sulfuric acid, heat(f) Sodium amide (NaNH2)arrow_forwardThe hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?arrow_forward
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