ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 15, Problem 15.21P
Which
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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?
4-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
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H3O+
Chapter 15 Solutions
ORGANIC CHEMISTRY
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Problem 15.6 Using mechanism 15.1 as guide, write...Ch. 15 - Prob. 15.7PCh. 15 - Problem 15.8 Which bond in the each compound is...Ch. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Draw the products of each reaction.
a. b. c.
Ch. 15 - Draw all constitutional isomers formed when each...Ch. 15 - Draw the structure of the four allylic halides...Ch. 15 - Problem 15.20 Which compounds can be prepared in...Ch. 15 - Which CH bond is most readily cleaved in linolenic...Ch. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Problem 15.24 When adds to under radical...Ch. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Problem 15.27 Draw the steps of the mechanism that...Ch. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - 15.35 What is the major monobromination product...Ch. 15 - Prob. 15.36PCh. 15 - 15.37 What alkane is needed to make each alkyl...Ch. 15 - 15.38 Which alkyl halides can be prepared in good...Ch. 15 - Prob. 15.39PCh. 15 - 15.40 Explain why radical bromination of p-xylene...Ch. 15 - a. What product(s) (excluding stereoisomers) are...Ch. 15 - Prob. 15.42PCh. 15 - 15.43 Draw the products formed when each alkene is...Ch. 15 - 15.44 Draw all constitutional isomers formed when...Ch. 15 - 15.45 Draw the organic products formed in each...Ch. 15 - Prob. 15.46PCh. 15 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 15 - 15.48 Draw the products formed in each reaction...Ch. 15 - Prob. 15.49PCh. 15 - 15.50 Draw all the monochlorination products that...Ch. 15 - Prob. 15.51PCh. 15 - 15.52 (a) Draw the products (including...Ch. 15 - 15.53 Consider the following bromination: .
a....Ch. 15 - 15.54 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 15.55PCh. 15 - Prob. 15.56PCh. 15 - 15.57 Devise a synthesis of each compound from...Ch. 15 - Prob. 15.58PCh. 15 - Prob. 15.59PCh. 15 - 15.60 Devise a synthesis of each compound using ...Ch. 15 - Prob. 15.61PCh. 15 - Prob. 15.62PCh. 15 - 15.63 As described in Section 9.16, the...Ch. 15 - 15.64 Ethers are oxidized with to form...Ch. 15 - Prob. 15.65PCh. 15 - Prob. 15.66PCh. 15 - 15.67 In cells, vitamin C exists largely as its...Ch. 15 - What monomer is needed to form each...Ch. 15 - Prob. 15.69PCh. 15 - Prob. 15.70PCh. 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. 15.73PCh. 15 - 15.74 A and B, isomers of molecular formula , are...Ch. 15 - Prob. 15.75PCh. 15 - 15.76 Draw a stepwise mechanism for the...Ch. 15 - Prob. 15.77PCh. 15 - Prob. 15.78PCh. 15 - Prob. 15.79P
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- This is a reduction reaction. Two hydrogens and two electrons are used to reduce the ketone to an alcohol. Draw out the structures of NaBD4 and EtOH. What is their role in this reaction? Draw the product of the reaction. What advantage is there to using these reducing agents instead of hydrogenation reagents (H2, metal catalyst)?arrow_forwardFor the substitution reaction. Draw the structure of the intermediate that forms in the rate determining step. Он HBr (aq) Brarrow_forward20 MgBr +0=C=O Ⓡ product HCLH₂O → ??arrow_forward
- Use 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_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_forwardDraw the skeletal ("line") structure of the smallest organic molecule that produces sodium hexanoate when reacted with NaOH. Click and drag to start drawing a structure. ✗ D: ☑ ค 5arrow_forward
- Draw the structures of four six-carbon alkenes that form the same product, whether they react with HBr in the presence of a peroxide or with HBr in the absence of a peroxidearrow_forwardThe electrophile in the reaction between Br2 and an alkene is the ion.arrow_forwardDE CH 2 step PG PG= Protecting Grouparrow_forward
- Part A: Draw the line-angle formula for methyl propanoate Part B: Draw the product of the reaction of ethylmethylamine with water Part C: Draw the product of the neutralization of ethylmethylamine with HBrarrow_forwardNitration of an aromatic ring involves an electrophilic substitution reaction. Draw the structure of the electrophile that is attacked by the aromatic ring and the intermediate formed after attachment of the electrophile to the ring. Be sure to show formal charges.arrow_forwardDraw the three possible resonance structures for an acid bromide, RCOBr. Then decide if RCOBr is more or less stabilized by resonance than a carboxylic acid (RCOOH).arrow_forward
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