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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CH₂-CH₂-CH₂-C-OH
butanoic acid
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3-methylpentanoic acid
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B) CHICHICIO
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Draw a condensed structural diagram for each carboxylic acid
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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 ?
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 formulas of the following compounds:(a) 2,3-Dimethylpentanal(b) 1,3-Dibromopropanone(c) 4-hydroxy-4-methylhexan-2-onearrow_forwardGive reasons for the following :(i) Phenol is more acidic than methanol.(ii) The C—O—H bond angle in alcohols is slightly less than the tetrahedral angle (190°28′).(iii) (CH3)3C—O—CH3 on reaction with HI gives (CH3)3C—I and CH3—OH as the main products and not (CH3)3C—OH and CH3—I.arrow_forwardDraw structures corresponding to the following names: (a) 3-hydroxyhexanoic acid (b) 2-iodo-2-methyloctanoic acid (c) 2-butynoic acid (d) 5-ethyl-6-oxoheptanoic acid (e) o-Hydroxybenzoic acid (f) cis-3-isopropylcyclohexanecarboxylic acidarrow_forward
- 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 ketonearrow_forwardDraw structures corresponding to the following IUPAC names: (a) cis-1,2-Cyclohexanedicarboxylic acid (b) Heptanedioic acid (c) 2-Hexen-4-ynoic acidarrow_forwardDraw 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_forward
- Predict the products of the following acid-base reactions. If the equilibrium would not result in the formation of appreciable amounts of products, you should so indicate. In each case label the stronger acid, the stronger base, the weaker acid, and the weaker base: (a) CH3CH=CH2 + NANH2 (d) CH3C=C: + CH;CH2OH → (e) CH3C=C:- + NH¾CI – | (b) CH;C=CH + NaNH2 (c) CH3CH2CH3 + NANH2 → | HASarrow_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_forwardPlease draw the skeletal formula of the following compounds: (A) Isobutyraldehyde (B) α-Ethyl-γ-methoxycaproaldehyde (C) 6-Hydroxyhexanal (D) 2,4-Pentanedione (E)3-Cyano-7-oxoheptanoic acidarrow_forward
- 17) 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_forwardHow could you convert butanenitrile into the following compounds? Write each step showing the reagents needed. (a) 1-Butanol (b) Butylaminearrow_forwardHow could you convert butanoic acid into the following compounds? Write each step showing the reagents needed. (a) 1-Butanol (b) 1-Bromobutane (c) 1-Butenearrow_forward
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