Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 20.1, Problem 2P
Draw structures corresponding to the following IUPAC names:
(a) 2, 3-Dimethylhexanoic acid
(b) 4-Methylpentanoic acid
(c) trans-1, 2-Cyclobutanedicarboxylic acid
(d) o-Hydroxybenzoic acid
(e) (9Z, 12Z)-9, 12-Octadecadienoic acid
(f) 2-Pentenenitrile
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1. Draw structures corresponding to the following IUPAC names:
(a) 4-Methylpentanoic acid
(b) o-Hydroxybenzoic acid
(c) 2,2-Dimethylpropanoyl chloride
(d) trans-2-Methylcyclohexanecarboxamide
(e) p-Methylbenzoic anhydride
(f) p-Bromobenzonitrile
Write the products of the following acid-base reactions:
(a) CH3OH + H2SO4 ² ?
(b) CH3OH + NANH2 2 ?
(c) CH3NH3+ Cl- + NaOH ?
Which of the following molecules
(1)
(2)
CH,0-ČCH,CH,
CH,CH,CH
(3) О—С—Он
(4)
OH
CH,CHCH,CH,
(5) CH,-NH
would:
neutralize NaOH
neutralize HCI
yields an alcohol and an organic acid when hydrolyzed
is easily oxidized to an acid
would be classifed as aromatic
could be oxidized to give a ketone
Chapter 20 Solutions
Organic Chemistry
Ch. 20.1 - Give IUPAC names for the following compounds:Ch. 20.1 - Draw structures corresponding to the following...Ch. 20.2 - Prob. 3PCh. 20.2 - The Ka for dichloroacetic acid is 3.32 Ă— 10-2....Ch. 20.3 - Calculate the percentages of dissociated and...Ch. 20.4 - Which would you expect to be a stronger acid, the...Ch. 20.4 - Dicarboxylic acids have two dissociation...Ch. 20.4 - The pKa of p-cyclopropylbenzoic acid is 4.45. Is...Ch. 20.4 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.6 - Prob. 11PCh. 20.6 - How might you carry out the following...Ch. 20.7 - Prob. 13PCh. 20.7 - Prob. 14PCh. 20.8 - Cyclopentanecarboxylic acid and...Ch. 20.8 - Prob. 16PCh. 20.SE - Prob. 17VCCh. 20.SE - Prob. 18VCCh. 20.SE - The following carboxylic acid can’t be prepared...Ch. 20.SE - Electrostatic potential maps of anisole and...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Prob. 23MPCh. 20.SE - Predict the product(s) and provide the complete...Ch. 20.SE - Acid-catalyzed hydrolysis of a nitrile to give a...Ch. 20.SE - Prob. 26MPCh. 20.SE - Naturally occurring compounds called cyanogenic...Ch. 20.SE - 2-Bromo-6, 6-dimethylcyclohexanone gives 2,...Ch. 20.SE - Naturally occurring compounds called terpenoids,...Ch. 20.SE - In the Ritter reaction, an alkene reacts with a...Ch. 20.SE - Give IUPAC names for the following compounds:Ch. 20.SE - Prob. 32APCh. 20.SE - Prob. 33APCh. 20.SE - Prob. 34APCh. 20.SE - Prob. 35APCh. 20.SE - Prob. 36APCh. 20.SE - Prob. 37APCh. 20.SE - Prob. 38APCh. 20.SE - Calculate the Ka's for the following acids: (a)...Ch. 20.SE - Thioglycolic acid, HSCH2CO2H, a substance used in...Ch. 20.SE - Prob. 41APCh. 20.SE - Prob. 42APCh. 20.SE - How could you convert butanoic acid into the...Ch. 20.SE - How could you convert each of the following...Ch. 20.SE - How could you convert butanenitrile into the...Ch. 20.SE - How would you prepare the following compounds from...Ch. 20.SE - Prob. 47APCh. 20.SE - Using 13CO2 as your only source of labeled carbon,...Ch. 20.SE - Prob. 49APCh. 20.SE - Which method-Grignard carboxylation or nitrile...Ch. 20.SE - Prob. 51APCh. 20.SE - Prob. 52APCh. 20.SE - Propose a structure for a compound C6H12O2 that...Ch. 20.SE - Prob. 54APCh. 20.SE - How would you use NMR (either 13C or 1H) to...Ch. 20.SE - Prob. 56APCh. 20.SE - A chemist in need of 2,2-dimethylpentanoic acid...Ch. 20.SE - Prob. 58APCh. 20.SE - Prob. 59APCh. 20.SE - Prob. 60APCh. 20.SE - Prob. 61APCh. 20.SE - Prob. 62APCh. 20.SE - Prob. 63APCh. 20.SE - The following pKa values have been measured....Ch. 20.SE - Identify the missing reagents a-f in the following...Ch. 20.SE - Propose a structure for a compound, C4H7N, that...Ch. 20.SE - Prob. 67APCh. 20.SE - The 1H and 13C NMR spectra below belong to a...Ch. 20.SE - Propose structures for carboxylic acids that show...Ch. 20.SE - Carboxylic acids having a second carbonyl group...
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- Draw the structural formula for the following molecules : (a) (b) (c) (d) (e) (f) (g) 1,2-dimethylcyclobutane 2,2-dimethylpropane 1,4-hexadiene toluene ortho-hydroxybenzoic acid methylcyclopropane propanal 2.arrow_forwardIn each of the following reactions, two possible organic products can be formed. Draw both organic products in each case and then circle the one formed in greatest quantity in each case. HC (a) 1) NaH, 2) acid (b) CH,CH,OH (c) CH,CH,OH NH2 (d) Oarrow_forward2. Draw structures corresponding to the following names: (a) 2,3-Dimethylhexanoic acid (b) 4-Methylpentanoic acid (c) o-Hydroxybenzoic acid (d) trans-Cyclobutane-1,2-dicarboxylic acidarrow_forward
- Draw compounds that contain the following: (a) A primary alcohol (c) A secondary thiol (c) An isopropyl group (b) A tertiary nitrile (d) A quaternary carbonarrow_forwardWrite the reagent or draw structures of the starting material or organic product(s) in the following reactions. If more than one product is formed, identify the major product where possible. (a) (b) HO OH OH H2SO4 ? Cl₂ ? FeCl3arrow_forward17) Which of the following compounds does not have the molecular formula C6H140? (a) 1-hexanol (b) 2-hexanol (c) 3-methyl-2-pentanol (d) 3-methyl-3-pentanol (e) Cyclohexanolarrow_forward
- Draw structural formulas for the following the compounds: (a) Cis-1,3-diphenylcyclohexane (b) 5-phenylpentanoic acid (c) 3,4-dibromo-N,N-dimethylanilinearrow_forwardDraw the structure of the following compounds which parent names have been traced to a common name; (a)5-methyl-4-nitroimidazole (b)2-chloro-4-methoxythiazole.arrow_forwardWhat is the major organic product of the following reaction? (a) (b) NaBH4 CH3CH₂OH ? (c) (d) OHarrow_forward
- Give an IUPAC and common name for each of the following naturally occurring carboxylic acids: (a) CH3CH(OH)CO2H (lactic acid); (b) HOCH2CH2C(OH)(CH3)CH2CO2H (mevalonic acid).arrow_forward1.Name and draw the products of each reaction. (a) 1-propanol + hydrobromic acid → HSO (b) 1-pentanol A HSO (c) N-propylmethanamide + water (d) 3-methyl oct-2-ene + hydrochloric acid - (e) 2-fluoro-2-phenyl butanoic acid + ethanolarrow_forward14. What is the IUPAC name for the following compound? NH- (a) propyl propanamide (b) propyl propanoate (c) N-propylptopanamine. (d) N, N-propylpropanamide (e) N-propxlpropanamidearrow_forward
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