Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 19.SE, Problem 57AP
Draw structures of compounds that fit the following descriptions:
a) An α, β-unsaturated
b) An α-diketone
c) An
d) A diene
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It is not A or C
Which of the isomeric C4H₁0O alcohols can be prepared by hydrogenation of aldehydes?
Which can be prepared by hydrogenation of ketones? Which cannot be prepared by
hydrogenation of a carbonyl compound?
Glucose, C6H12O6, contains an aldehyde group but exist predominantly in the form of the cyclic hemiacetal show below.
A cyclic hemiacetal is formed when the —OH group of one carbon bonds to the carbonyl group of another carbon. Identify which carbon provides the —OH group and which provides the —CHO? Give a functional isomer of glucose and draw its structure.
Chapter 19 Solutions
Organic Chemistry
Ch. 19.1 - Prob. 1PCh. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3PCh. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7PCh. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9PCh. 19.8 - Show the products you would obtain by...
Ch. 19.8 - Prob. 11PCh. 19.8 - Prob. 12PCh. 19.9 - Prob. 13PCh. 19.10 - Prob. 14PCh. 19.10 - Prob. 15PCh. 19.11 - What carbonyl compound and what phosphorus ylide...Ch. 19.11 - -Carotene, a yellow food-coloring agent and...Ch. 19.12 - Prob. 18PCh. 19.12 - Prob. 19PCh. 19.13 - Prob. 20PCh. 19.13 - Treatment of 2-cyclohexenone with HCN/KCN yields a...Ch. 19.13 - How might conjugate addition reactions of lithium...Ch. 19.14 - How might you use IR spectroscopy to determine...Ch. 19.14 - Prob. 24PCh. 19.14 - Prob. 25PCh. 19.14 - Prob. 26PCh. 19.SE - Each of the following substances can be prepared...Ch. 19.SE - Prob. 28VCCh. 19.SE - Prob. 29VCCh. 19.SE - Prob. 30MPCh. 19.SE - Prob. 31MPCh. 19.SE - Prob. 32MPCh. 19.SE - Prob. 33MPCh. 19.SE - Prob. 34MPCh. 19.SE - Prob. 35MPCh. 19.SE - It is not uncommon for organic chemists to prepare...Ch. 19.SE - Prob. 37MPCh. 19.SE - Prob. 38MPCh. 19.SE - Prob. 39MPCh. 19.SE - Prob. 40MPCh. 19.SE - Aldehydes and ketones react with thiols to yield...Ch. 19.SE - Prob. 42MPCh. 19.SE - When cyclohexanone is heated in the presence of a...Ch. 19.SE - Prob. 44MPCh. 19.SE - The Meerwein-Ponndorf-Verley reaction involves...Ch. 19.SE - Propose a mechanism to account for the formation...Ch. 19.SE - Prob. 47MPCh. 19.SE - Prob. 48MPCh. 19.SE - Treatment of an , -unsaturated ketone with basic...Ch. 19.SE - Prob. 50MPCh. 19.SE - Prob. 51MPCh. 19.SE - Prob. 52MPCh. 19.SE - Prob. 53MPCh. 19.SE - Prob. 54APCh. 19.SE - Draw and name the seven aldehydes and ketones with...Ch. 19.SE - Give IUPAC names for the following compounds:Ch. 19.SE - Draw structures of compounds that fit the...Ch. 19.SE - Predict the products of the reaction of (1)...Ch. 19.SE - Show how you might use a Wittig reaction to...Ch. 19.SE - How would you use a Grignard reaction on an...Ch. 19.SE - Prob. 61APCh. 19.SE - Prob. 62APCh. 19.SE - How would you synthesize the following substances...Ch. 19.SE - Carvone is the major constituent of spearmint oil....Ch. 19.SE - How would you synthesize the following compounds...Ch. 19.SE - At what position would you expect to observe IR...Ch. 19.SE - Acidcatalyzed dehydration of...Ch. 19.SE - Choose the structure that best fits the IR...Ch. 19.SE - Propose structures for molecules that meet the...Ch. 19.SE - Prob. 70APCh. 19.SE - Prob. 71APCh. 19.SE - When 4hydroxybutanal is treated with methanol in...Ch. 19.SE - Prob. 73APCh. 19.SE - Prob. 74APCh. 19.SE - Prob. 75APCh. 19.SE - Prob. 76APCh. 19.SE - Prob. 77APCh. 19.SE - Tamoxifen is a drug used in the treatment of...Ch. 19.SE - Compound A, MW 86, shows an IR absorption at 1730...Ch. 19.SE - Compound B is isomeric with A (Problem 19-79) and...Ch. 19.SE - The 1HNMR spectrum shown is that of a compound...Ch. 19.SE - Prob. 82APCh. 19.SE - Propose structures for ketones or aldehydes that...Ch. 19.SE - Prob. 84APCh. 19.SE - Prob. 85APCh. 19.SE - The proton and carbon NMR spectra for each of...Ch. 19.SE - The proton NMR spectrum for a compound with...
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- Glucose, C6H12O6, contains an aldehyde group but exist predominantly in the form of the cyclic hemiacetal show below. A cyclic hemiacetal is formed when the —OH group of one carbon bonds to the carbonyl group of another carbon. Identify which carbon provides the —OH group and which provides the —CHO? Give a functional isomer of glucose and draw its structure.arrow_forwardCompound A has the molecular formula C7H12. Hydrogenation of compound A produces 2-methylhexane. Hydroboration-oxidation of compound A produces an aldehyde. Draw the structure of compound A.arrow_forward1) The acid-catalyzed dehydration of 2-methyl-2-butanol yields two alkene products, what are the names of the two alkenes? 2) which of the two alkenes is the major product?arrow_forward
- Draw the following structures: a) N-cyclopropyl-3-methylhexanamide b) phenylpropanoate c) 3-chloro-2-isopropoxynonanearrow_forwardName the 7 aldehydes and ketones with formulaC5H10Oarrow_forwardThere are several aromatic compounds with the formula C8H9Cl. Draw the ones that have a monosubstituted ring.arrow_forward
- Draw the structures of the two isomers with the molecular formula C₂H 0 that are carbonyl compounds and label as an aldehyde or a ketone.arrow_forward#2arrow_forwardSuppose propene (CH2=CH-CH3) is the hydrocarbon that reacts with the hydroxyl radical ∙OH. Beginning with addition of ∙OH, write the set of chemical reactions that ultimately produces an aldehyde. What is this final aldehyde?arrow_forward
- Draw an isomer of C5H10O that contains a ketonearrow_forwardWhich one(s) of the following reactions produce propan-1-ol? A) the alkaline hydrolysis of 1-chloropropane B) the acid hydrolysis of propyl methanoate C) the acid hydrolysis of propanenitrilearrow_forwardThe acid-catalyzed dehydration of 2,3-dimethyl-3-pentanol yields three alkene products. What are the names of the three alkenes? Which of the three alkenes is the major product?arrow_forward
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