ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 21, Problem 38P
Acyclovir is an effective antiviral agent used to treat the herpes simplex virus.(a) Draw the enol form of acyclovir, and explain why it is
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Acyclovir is an effective antiviral agent used to treat the herpes simplex virus. (a) Draw the enol form of acyclovir, and explain why it is aromatic. (b) Why is acyclovir typically drawn in its keto form, despite the fact that its enol is aromatic?
(a) Draw two different enol tautomers of 2-methylcyclohexanone. (b) Draw two constitutional
isomers that are not tautomers, but contain a C=C and an OH group.
2-methylcyclohexanone
(c)
Draw the structure of the hemi-acetal and acetal formed when cyclohexanone is
combined with methanol in the presence of catalytic acid.
Chapter 21 Solutions
ORGANIC CHEMISTRY
Ch. 21.2 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 21.2 - Problem 23.3 When phenylacetaldehyde is dissolved...Ch. 21.3 - Prob. 5PCh. 21.3 - Problem 23.5 Which bonds in the following...Ch. 21.3 - Prob. 7PCh. 21.3 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.4 - Prob. 10PCh. 21.5 - Prob. 11PCh. 21.7 - Problem 23.11 Draw the products of each...
Ch. 21.7 - Problem 23.12 Draw the products of each reaction....Ch. 21.7 - Prob. 14PCh. 21.7 - Prob. 15PCh. 21.8 - Prob. 16PCh. 21.8 - Prob. 17PCh. 21.8 - Prob. 18PCh. 21.8 - Problem 23.18 How can pentan-2-one be converted...Ch. 21.8 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 21.9 - Problem 23.20 Which of the following compounds...Ch. 21.9 - Problem 23.21 Draw the products of each...Ch. 21.9 - Prob. 23PCh. 21.9 - Prob. 24PCh. 21.9 - Prob. 25PCh. 21.10 - Prob. 26PCh. 21.10 - Prob. 27PCh. 21.10 - Prob. 28PCh. 21.10 - Prob. 29PCh. 21 - 23.29 Draw enol tautomer(s) for each compound....Ch. 21 - 22.30 The cis ketone A is isomerized to a trans...Ch. 21 - 23.31 Draw enol tautomer(s) for each compound.
...Ch. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - 23.35 Rank the labeled protons in each compound in...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - 23.38 Acyclovir is an effective antiviral agent...Ch. 21 - 23.39 Explain why forms two different alkylation...Ch. 21 - Prob. 40PCh. 21 - 23.42 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - 23.45 Devise a synthesis of valproic acid , a...Ch. 21 - Prob. 57PCh. 21 - 23.57 Draw a stepwise mechanism showing how two...Ch. 21 - 23.58 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 65PCh. 21 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...
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- Why is cycloprop-2-enone more polar than cyclopropanone? a) Cycloprop-2-enone is more polar because, as drawn, it is aromatic. b) Cycloprop-2-enone is more polar because it has a resonance form that possesses an aromatic cation. c) Cycloprop-2-enone is more polar because it has a resonance form that possesses an aromatic anion.arrow_forwardConsider the tetracyclic compound with rings labeled A–D. (a) Which ring is the most reactive in electrophilic aromatic substitution? (b) Which ring is the least reactive in electrophilic aromatic substitution?arrow_forwardDraw all of the substitution and elimination products formed from the given alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate the stereochemistry around the stereogenic centers present in the products, as well as the mechanism by which each product is formed.arrow_forward
- a) What is the major alkene formed when A is dehydrated with H2SO4? (b) What is the major alkene formed when A is treated with POCl3 and pyridine? Explain why the major product is different in these reactions.arrow_forwardDraw the product(s) formed when A is treated with each reagent. (a) NaBH4, CH3OH (b) [1] LiAlH4; [2] H2O (c) CH3CH2MgBr; [2] H2Oarrow_forwardCompound A has molecular formula C7H15B.. Treatment of compound A with sodium ethoxide yields only one elimination product (compound B) and no substitution products. When compound B is treated with dilute sulfuric acid, compound C is obtained, which has molecular formula C7H160. Draw the structures of compounds A, B, and C.arrow_forward
- β-Vetivone is isolated from vetiver, a perennial grass that yields a variety of compounds used in traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to β-vetivone by a two-step process:Michael reaction, followed by intramolecular aldol reaction. (a) What Michael acceptor is needed for the conjugate addition? (See Problem 23.61 for another method to form the bicyclic ring system of β-vetivone.) (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.arrow_forwardDraw the structure of (S)-citalopram, a drug used to treat depression and anxiety that is much more potent than its R enantiomer.arrow_forward(1) Which of the following choices is the identity ROH? (2) Which of the following choices if the identity of CARBONYL?arrow_forward
- (a) Add curved arrows for each step to show how A is converted to the epoxy ketone C. (b) Classify the conversion of A to C as a substitution, elimination, or addition. (c) Draw one additional resonance structure for B.arrow_forwardWhich is more acidic, p-methylphenol or phenol? why? Why is water more acidic than ethanol but slightly less acidic than methanol? Explain the acidity trend of alcohols: 1>2 > 3arrow_forwardβ-Vetivone is isolated from vetiver, a perennial grass that yields a variety ofcompounds used in traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to β-vetivone by a two-step process: Michael reaction, followed by intramolecular aldol reaction. (a) What Michael acceptor is needed for the conjugate addition? (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.arrow_forward
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