Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 19.SE, Problem 65AP
How would you synthesize the following compounds from cyclohexanone?
a) 1-Methylcyclohexene
b) 2-Phenvlcyclohexanone
c) cis-1, 2-Cyclohexanediol
d) 1-Cyclohexylcyclohexanol
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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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- 30) The name of OHCH2CH2CHCOOH is CH3 A) 2-carboxy-butanol B) 1-hydroxy-3 methylbutanoic acid C) 4-hydroxy-2-methylbutanoic acid D) 4-hydroxy-2-methylpropionic acid E) 1-hydroxy-3-methylbutyric acidarrow_forwardWhich of the following molecules gives a condensation reaction with benzaldehyde? a) methylbenzaldehyde b) 2,2-dimethylpropanoic acid c) 3-methylbenzaldehyde d) 4-chlorobenzaldehyde e) 3-methylbutanoic acidarrow_forwardWhat is the reduction product of the following compound with H2/Pd? A 2-propyl-1-cyclohexanol B 2-propenyl-1-cyclohexanol C2-propylcyclohexanone D 1-propyl-2-cyclohexanol What is the oxidation product of this compound? H' A ethanoic acid acetic acid propanoic acid D propanone What is the oxidation product of this compound? A 3,4-dimethylpentanoic acid B 2,3-dimethylpentanoic acid C2,3-dimethylpentanone 3,4-dimethylpentanonearrow_forward
- A) nthyl benzene ketone B) ethyl phenyl ketone C) ethane benzene ketone D) ethane phenyl ketone E) phenyl propanonearrow_forwardThe acetal shown below is composed of which of the following original compounds?arrow_forwardThe IUPAC name is: HO a) l,,4-trimethylcyclohexano) b) I,4,4 - trimethyl cyclohexanol C) 3,3,6-te?methyl cyclohexano) d) 2,5,5-trimethylayclohexano) The IUPAC name 9s: OH Br a) 6-bromo-2-methylcyclohew-1-en-3-01 b) 4 -bromo- a- methylycohen-2-en -\-0l C) S-bromo -1-methyicgclohex-l- en-2-01 d) 3-bromo-l-methylcyclohex-1-en-6-01 e) s-bromo-2-methylcyclohexol- en -2-01arrow_forward
- What is the correct IUPAC name....arrow_forward8. The following compounds are named incorrectly according to IUPAC rules. Draw out the condensed structural formula for each compound and name it correctly. a) 2-propyl-3-butanol b) 2,5-diethyl-1-pentanone c) 3,3-dimethyl-1-propanal d) 1-ethyl-3-cyclohexanolarrow_forwardName the following organic compound: CH₂ CH₂ H3C CH₂ OH O 2-oxo-5-pentanol O 4-oxo-1-pentanol O 5-hydroxy-2-pentanone O hydroxypentanone O 1-hydroxy-4-pentanonearrow_forward
- Alcohols undergo dehydration reactions in the presence of an acid catalyst. Which of the following compounds yields only a single alkene product upon dehydration?arrow_forward8) What is the correct name of the molecule HO a) 5-hydroxy pentanal b) 4-carbonyl-1-butanal c) 4-oxo-1-butanol d) 4-hydroxybutane carbaldehyde e) 4-hydroxybutanal 왜?arrow_forwardWhat functional group is shown here: CH3CH₂COOH carboxylic acid ether alcohol ketone aldehydearrow_forward
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