Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 15, Problem 15.22P
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OH
1. NaOH, EtOH
2. n-BuBr
A nucleophilic substitution reaction is a frequently used method to convert one functional group
into another. A nucleophile is mixed with an electrophile and the nucleophile replaces the leaving group
to produce a new compound. In this experiment, a weak nucleophile (2-naphthol) is converted into a
strong nucleophile by deprotonation with sodium hydroxide. Then this strong nucleophile, now with a
negative charge, reacts with alkyl halide to yield an ether, 2-butoxynaphthalene. 2-butoxynaphthalene is
a flavoring agent that has strong fruit smell like raspberry and strawberry.
How does the first step in the reaction of propene with Br2 differ from the first step in the reaction of propene with HBr?
An electron-deficient carbon atom reacts with a nucleophile, symbolized as: Nu−. Define this ?
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Draw the product formed when a chlorine atom (Cl)...Ch. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Problem 15.6 Using mechanism 15.1 as guide, write...Ch. 15 - Calculate m0 for the two propagation steps in the...Ch. 15 - Prob. 15.8PCh. 15 - Problem 15.8 Which bond in the each compound is...Ch. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Synthesize each compound from (CH3)3CH. a....Ch. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Draw all constitutional isomers formed when each...Ch. 15 - Draw the structure of the four allylic halides...Ch. 15 - Which compounds can be prepared in good yield by...Ch. 15 - Which CH bond is most readily cleaved in linolenic...Ch. 15 - Prob. 15.23PCh. 15 - Draw the products formed when each alkene is...Ch. 15 - Problem 15.24 When adds to under radical...Ch. 15 - Prob. 15.26PCh. 15 - Draw an energy diagram for the two propagation...Ch. 15 - Prob. 15.28PCh. 15 - Problem 15.27 Draw the steps of the mechanism that...Ch. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Why is a benzylic CH bond labeled in red unusually...Ch. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - What alkane is needed to make each alkyl halide by...Ch. 15 - Which alkyl halides can be prepared in good yield...Ch. 15 - Prob. 15.41PCh. 15 - 15.40 Explain why radical bromination of p-xylene...Ch. 15 - a. What product(s) (excluding stereoisomers) are...Ch. 15 - Prob. 15.44PCh. 15 - Prob. 15.45PCh. 15 - Prob. 15.46PCh. 15 - 15.44 Draw all constitutional isomers formed when...Ch. 15 - Draw the organic products formed in each reaction....Ch. 15 - Prob. 15.49PCh. 15 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 15 - Prob. 15.51PCh. 15 - Prob. 15.52PCh. 15 - Prob. 15.53PCh. 15 - Prob. 15.54PCh. 15 - 15.53 Consider the following bromination: .
a....Ch. 15 - 15.54 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 15.57PCh. 15 - An alternative mechanism for the propagation steps...Ch. 15 - Prob. 15.59PCh. 15 - Prob. 15.60PCh. 15 - Devise a synthesis of each compound from...Ch. 15 - Devise a synthesis of each target compound from...Ch. 15 - Devisea synthesis of each target compound from the...Ch. 15 - Devise a synthesis of each compound using CH3CH3...Ch. 15 - Prob. 15.65PCh. 15 - 15.63 As described in Section 9.16, the...Ch. 15 - 15.64 Ethers are oxidized with to form...Ch. 15 - Prob. 15.68PCh. 15 - Prob. 15.69PCh. 15 - 15.67 In cells, vitamin C exists largely as its...Ch. 15 - What monomer is needed to form each...Ch. 15 - Prob. 15.72PCh. 15 - Prob. 15.73PCh. 15 - 15.71 Draw a stepwise mechanism for the following...Ch. 15 - 15.72 As we will learn in Chapter 30, styrene...Ch. 15 - Prob. 15.76PCh. 15 - 15.74 A and B, isomers of molecular formula , are...Ch. 15 - Prob. 15.78PCh. 15 - Radical chlorination of CH3CH3 forms two minor...Ch. 15 - 15.76 Draw a stepwise mechanism for the...Ch. 15 - Prob. 15.81PCh. 15 - Prob. 15.82PCh. 15 - Prob. 15.83P
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- 3. Why did breaking the P-C single bond lead to the formation of 2 species containing a free radical (ie. where did those 2 electrons come from)? 4. Do you think the photoinitiator 2-hydroxy-2-methylpropiophenone would require a shorter or longer wavelength of light to create a free radical? Explain your answer using the table provided in question #2 (be specific). The structure of 2-hydroxy-2- methylpropiophenone is shown below. CH3 Figure 5: Structure of 2-hydroxy-2- methylpropiophenone. The wavy line shows OH the bond that is photo-sensitive (ie. the bond that will be broken by light). (Taken from Tehfe et al. 2013, http://www.mdpi.com/2076- 3417/3/2/490/htm) ČH3 5. Why is the PEGDA monomer soluble in water, but the polymer is not? In other words, why do you think forming a large molecule would lead to the formation of a solid? (Hint: think about the movement of molecules in a liquid vs solid phase). 6. Thinking about the octet rule, why do you think many free radicals are very…arrow_forwardWhen propene reacts with gaseous hydrogen bromide, HBr, two products, 1-bromopropane and 2-bromopropane are formed. The reaction is a two-step process in which the electrophilic attack occurs in the first step. Identify the electrophile in this reaction Draw a diagram showing the first step of the reaction that leads to the production of 2-bromopropane.arrow_forward4-pyranone will readily undergo an acid-base reaction. Identify the reaction conditions that will result in the formation of an aromatic product. Then, draw the aromatic resonance product structure. Include all lone pairs in your structure. Ignore inorganic byproducts. H3O+arrow_forward
- Which C–H bond is most readily cleaved in linoleic acid? Draw all possible resonance structures for the resulting radical. Draw all the hydroperoxides formed by reaction of this resonance-stabilized radical with O2.arrow_forwardUse a sheet of paper to answer the following question. Take a picture of your answers and attach to this assignment. Draw the mechanism for the acid-catalyzed reaction of acetic acid (ethanoic acid) with the methanol to yield methyl acetate (methyl ethanoate). O O HCI H3C + CH3OH OH H3C OCH 3 + H₂Oarrow_forwardWhat is the product or products of the nucleophilic substitution reaction 4-bromocyclohexane + NaCNarrow_forward
- Complete these nucleophilic substitution reactions. In each reaction, show all electron pairs on both the nucleophile and the leaving group.arrow_forward0 CH₂ → ?? If the above compound is subjected to combustion, what are the products? ethanoic acid +2-phenyl-ethene-1-ol 15CO₂ (g) + 5H₂0 (g) O 2-phenyl-ethyl-ethanoate + H₂O 20CO₂ (g) + 10H₂O(g) →?? CH, if the above compound was treated with H and H₂O what product will form?arrow_forwardDE CH 2 step PG PG= Protecting Grouparrow_forward
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