ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 15, Problem 15.24P
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A certain hydrocarbon had the molecular formula C18H30 and contained two triple bonds. Ozonolysis gave CH₂(CH₂)CO₂H and HO₂CCH₂CH₂CO₂H as the
only products. Draw a reasonable structure for this hydrocarbon.
Click and drag to start drawing a structure.
H3C
CH3
H3C
NA C→XT
Br
Br₂
CH₂Cl₂
H3C
Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic
intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂.
CH3
Br
In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion
to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the
bromonium ion so that a product with anti stereochemistry is formed.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Br
CH3
H3C
CH3
Which of the following is a chain propagation step in the free radical chlorination of methane?
· CH3 + Cl · → CH3CI
Cl2 2 Cl ·
CH4 + Cl HCl + · CH3
CH3 + CH4 CH4 + ·CH3
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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- For the substitution reaction. Draw the structure of the intermediate that forms in the rate determining step. Он HBr (aq) Brarrow_forwardDraw structures for the alkene (or alkenes) that gives the following reaction product.arrow_forwardIdentify the type of reaction mechanism. CH3CH2CHO + HCN→→ CH3CH2CH(OH)CN Nucleophilic Substitution Reaction Elimination Reaction Nucleophilic Addition Reactionarrow_forward
- Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. b) For the major elimination product obtained in 5a), which stereoisomer (cis or trans) is obtained in greater yield? Draw the two isomers and provide the names of the compounds.arrow_forwardDraw the neutral organic starting material that will react with Br₂ to form 2-(bromomethyl)tetrahydrofuran. Draw the neutral organic starting material. [= Br₂ CH₂Cl₂arrow_forwardIn the reaction given below, what type of reaction is used? n-Pentane → Isopentane нннн H ITH Н—С—с—С—с —О —Н Н—с—с— с-с—н ||| | H нн H Addition Elimination Substitution Rearrangementarrow_forward
- Define the Mechanism of the Radical Addition of HBr to an Alkene ?arrow_forward2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3 CH3CHCH₂CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. n [ ]# ?arrow_forward
- Identify the type of reaction mechanism. CH3CH2CH2OH + HI →→ CH3CH2CH2I + H2O Nucleophilic Substitution Reaction Nucleophilic Addition Reaction Elimination Reactionarrow_forward3. Please draw the most important (stable) resonance form of the carbonation that mediates the following reaction: OH H3O+ O 4. Draw the structure of the alkene isomer (with the molecular formula of C5H10) that is most reactive one in the addition reaction with Br₂.arrow_forwardDraw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown. Note: You do not need to draw any of the side products of the reaction, only the substitution product. + H₂O Cl + ☑ 5 C Click and drag to start drawing a structure.arrow_forward
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