Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 16.10, Problem 42P
(a)
Interpretation Introduction
Interpretation:
The product has to be predicted for the proceeding reaction with
(b)
Interpretation Introduction
Interpretation:
The reagent could be used to reduce only the keto group has to be predicted.
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Chapter 16 Solutions
Organic Chemistry (8th Edition)
Ch. 16.1 - Give two names for each of the following:Ch. 16.1 - Prob. 2PCh. 16.1 - Name the following:Ch. 16.2 - Prob. 4PCh. 16.4 - What products are formed when the following...Ch. 16.4 - We saw on the previous page that...Ch. 16.4 - a. How many stereoisomers are obtained from the...Ch. 16.4 - Prob. 9PCh. 16.4 - Write the mechanism for the reaction of acetyl...Ch. 16.4 - Prob. 11P
Ch. 16.4 - Show how the following compounds can be...Ch. 16.4 - Prob. 13PCh. 16.4 - Prob. 14PCh. 16.4 - In the mechanism for cyanohydrin formation, why is...Ch. 16.4 - Prob. 16PCh. 16.4 - Prob. 17PCh. 16.4 - Show two ways to convert an alkyl halide into a...Ch. 16.5 - Prob. 20PCh. 16.5 - Prob. 21PCh. 16.5 - Prob. 22PCh. 16.5 - Prob. 23PCh. 16.6 - Prob. 24PCh. 16.7 - What reducing agents should be used to obtain the...Ch. 16.7 - Prob. 26PCh. 16.8 - Prob. 27PCh. 16.8 - Prob. 28PCh. 16.8 - Prob. 29PCh. 16.8 - The pKa of protonated acetone is about 7.5. and...Ch. 16.8 - Prob. 31PCh. 16.8 - Prob. 32PCh. 16.8 - Prob. 33PCh. 16.8 - Excess ammonia must be used when a primary amine...Ch. 16.8 - The compounds commonly known as amino acids are...Ch. 16.9 - Hydration of an aldehyde is also catalyzed by...Ch. 16.9 - Which ketone forms the most hydrate in an aqueous...Ch. 16.9 - When trichloroacetaldehyde is dissolved in water,...Ch. 16.9 - Which of the following are a. hermiacetals? b....Ch. 16.9 - Prob. 40PCh. 16.9 - Explain why an acetal can be isolated but most...Ch. 16.10 - Prob. 42PCh. 16.10 - Prob. 43PCh. 16.10 - What products would be formed from the proceedings...Ch. 16.10 - a. In a six-step synthesis, what is the yield of...Ch. 16.10 - Show how each of the following compounds could be...Ch. 16.12 - Prob. 47PCh. 16.13 - Prob. 49PCh. 16.14 - Prob. 50PCh. 16.15 - Prob. 51PCh. 16.16 - Prob. 52PCh. 16 - Draw the structure for each of the following: a....Ch. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - Prob. 56PCh. 16 - a. Show the reagents required to form the primary...Ch. 16 - Prob. 58PCh. 16 - Prob. 59PCh. 16 - Using cyclohexanone as the starting material,...Ch. 16 - Propose a mechanism for each of the following...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Fill in the boxes:Ch. 16 - Prob. 64PCh. 16 - Identify A through O:Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - How many signals would the product of the...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Prob. 73PCh. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - Prob. 78PCh. 16 - Draw structure for A-D for each of the following:Ch. 16 - Prob. 80PCh. 16 - a. Propose a mechanism for the following reaction:...Ch. 16 - Prob. 82PCh. 16 - A compound gives the following IR spectrum. Upon...Ch. 16 - How can be following compounds be prepared from...Ch. 16 - Prob. 85PCh. 16 - Prob. 86PCh. 16 - Prob. 87PCh. 16 - In the presence of an acid catalyst, acetaldehyde...Ch. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - Prob. 91PCh. 16 - A compound reacts with methylmagnesium bromide...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Prob. 94PCh. 16 - The pKa values of the carboxylic acid groups of...Ch. 16 - The Baylis-Hillman reaction is a DABCO...Ch. 16 - Prob. 97PCh. 16 - Prob. 98P
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- From which starting materials can the product formed as a result of the following reaction be synthesized? A. Acetophenone and butanal B. Benzaldehyde and 3-pentanone C. Benzaldehyde and 2-pentanone D. Acetophenone and 2-butanonearrow_forwardWhat is the purpose of the first step of this reaction? OH 1. CH;CH,OH, H* 2. LIAIH4, Et,0 3. H*, H,0 Create an enolate on the a-carbon Reduce the ester Protect that aldehyde as an acetal Hydrolyze the ester to promote reactivity of the carboxylic acid derivativearrow_forwardWhich of the following compounds can be used to synthesize ethanoicpropanoic anhydride (CH;COOOCCH½CH3)? A. CH;COCI+ CH;CH2COO`Na* → B. CH;COOH +heat → C. CH3CH2CH2COCI + CH;COO Na* → D. A and Carrow_forward
- HCI is a byproduct of this reaction. Which statements are true? CH₂ . Cl₂ HCI prevents CH3 from acting as a leaving group HCI ensures that only one H of the CH3 is substituted by lowering the pH CH₂CI HCI can accelerate the reaction as it forms by catalyzing keto-enol tautomerism HCI can slow the reaction by enabling the formation of an enolate + HCIarrow_forwardd. Provide an arrow-pushing mechanism for the reaction. OH 1. NaOH 2. CH3CH₂ so acetaminophen phenacetinarrow_forwardLab 4: Reactions of Aldehydes and Ketones Reactions of Aldehydes and Ketones 2. Which of the following reagents or tests would you use to differentiate between sxiT CH,CH,CH, -Ċ-H and a. Iodoform b. Chromic acid c. Tollens' d. DNP e. More than one answer is correct. Explain your answer:arrow_forward
- 10. The Wolff-Kishner reaction, in which an aldehyde or ketone is treated with NH2NH2 and KOH, is: a) an oxidation c) an SN2 reaction b) a reduction d) a hydration 11. Which of these is most likely to dissolve in 5% NaOH? a) 1-decanol b) decanal c) decanoic acid d) 2-decanone 12. The following compound forms a cyclic hemiacetal all by itself. Draw the structure of that hemiacetal.arrow_forwardWhich of the following statements is INCORRECT? a. The electronegative oxygen atom of the α,β-unsaturated carbonyl compound withdraws electrons from the β-carbon leading to more electron-poor characteristic for the carbon than a typical alkene C=C bond. b. A carbon–oxygen double bond is structurally similar to a carbon–carbon double bond. c. Aldehyde and ketones usually react irreversibly with alcohols or water to yield acetals or vicinal diol respectively. d. The carbonyl carbon atom is sp2-hybridized and forms both sp2 σ-bond and a p π-bond to oxygen.arrow_forwardThe enolate derived from diethyl malonate reacts with a variety of electrophiles (not just alkyl halides) to form new carbon–carbon bonds. With this in mind, draw the products formed when Na+ −CH(CO2Et)2 reacts with each electrophile, followed by treatment with H2O.arrow_forward
- 8. Which of the following compounds would be expected to give a positive Tollens' test? a. 3-Pentanone b. Cyclohexanone c. 3-Methylbutanal d. Cyclopentanol e. 2,2-Dimethyl-1-pentanol f. Acetaldehydearrow_forwardWhich substrate will you use to synthesize 1-propanol from propanal? A.) NaBH₄ B.) O₃ C.) KMnO₄ D.) CH₃MgCl E.) None of the given answerarrow_forward1. Br₂, PBrg 2. H₂O H₂C OH H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br₂ reacts in an α- substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H3C :0: :0::Br: Br Br H3C CO-P H Br Brarrow_forward
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