Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 21.2, Problem 4P
When phenylacetaldehyde
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When phenylacetaldehyde (C6H5CH2CHO) is dissolved in D2O with added DCl, the hydrogen atoms α to the carbonyl are gradually replaced by deuterium atoms. Write a mechanism for this process that involves enols as intermediates.
H3C.
H3C.
CH3
nnc» XT
:OH
2 CH₂OH
HCI catalyst
Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is
used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by
loss of water to yield the product acetal.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
CH3
H3C
CH3OH
H3CQ OCH3
CH3
H3C.
H
HO: :OCH 3
CH3
46
When phenylacetaldehyde (C6H5CH2CHO) is dissolved in D2O with added DCl, the hydrogen atoms a to the carbonyl are gradually replaced by deuterium atoms. Write a mechanism for this process that involves enols as intermediates.
Chapter 21 Solutions
Organic Chemistry (6th Edition)
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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- Reaction of phenol with acetone in the presence of an acid catalyst gives a compound known as bisphenol A, which is used in the production of epoxy and polycarbonate resins (Section 29.5). Propose a mechanism for the formation of bisphenol Aarrow_forwardAn alkene is treated with OsO4 followed by H2O2. When the resulting diol is treated with HIO4, the only product obtained is an unsubstituted cyclic ketone with molecular formula C6H10O. What is the structure of the alkene?arrow_forwardWhen cis-2-decalone is dissolved in ether containing a trace of HCI, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. H H HCI cis-2-Decalone trans-2-Decalone Propose a mechanism for this isomerization and account for the fact that the trans iso- mer predominates at equilibrium.arrow_forward
- H3C- H3C. OCH 3 H3CO CH3 H Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions NA 2 CH₂OH HCI catalyst CH3 HỘ H3CQ H3C- H3CO CH3 H3C. OCH3 CH3 H₂O*: 45arrow_forwardDescribe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.arrow_forwardEthylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forward
- When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. Propose a mechanism for this isomerization and account for the fact that the trans isomer predominates at equilibrium.arrow_forwardClaisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads to the formation of a para-substituted product. Propose a mechanism for the following rearrangement.arrow_forwardA step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.arrow_forward
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