Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 10.SE, Problem 45AP
Interpretation Introduction
Interpretation:
Given that tertiary
Concept introduction:
The stability of free radicals is in the order benzyl > allyl > tertiary > secondary > primary > mehyl. The benzyl and allyl radicals are stabilized by resonance while tertiary, secondary and primary radicals are stabilized by hyperconjucation.
To explain:
Among (CH3)3CBr and H2C=CH C(CH3)2Br which will react faster.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
12) Use the curved arrow formalism to show the movement of electron pairs in the
following reaction and label each reactant as a nucleophile or an electrophile.
CHÍNH CHỊCH, + CO
Học Nha
CH₂CH₂CI
Identify the major product of this reaction of an alkene.
|
|||
OH
OH
1. Hg(OAc)2, H2O
2. NaBH4, NaOH
||
IV
ㅊ
OH
OH
Rank the following alkenes in order of increasing rate of hydrogenation.
11
OI<|||< IV < II
<|| < |||
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Prob. 1PCh. 10.1 - Draw structures corresponding to the following...Ch. 10.2 - Prob. 3PCh. 10.2 - Taking the relative reactivities of 1°, 2°, and...Ch. 10.4 - Prob. 5PCh. 10.4 - The major product of the reaction of...Ch. 10.4 - Prob. 7PCh. 10.5 - Prob. 8PCh. 10.6 - Prob. 9PCh. 10.6 - How might you replace a halogen substituent by a...
Ch. 10.7 - How would you carry out the following...Ch. 10.8 - Rank both sets of compounds in order of increasing...Ch. 10.8 - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 14VCCh. 10.SE - Prob. 15VCCh. 10.SE - Prob. 16VCCh. 10.SE - Draw the electron-pushing mechanism for each...Ch. 10.SE - Draw the electron-pushing mechanism for the...Ch. 10.SE - The formation of Br2 from NBS first involves the...Ch. 10.SE - In light of the fact that tertiary alkyl halides...Ch. 10.SE - Alkyl halides can be reduced to alkanes by a...Ch. 10.SE - Name the following alkyl halides:Ch. 10.SE - Prob. 23APCh. 10.SE - Draw and name all of the monochlorination products...Ch. 10.SE - How would you prepare the following compounds,...Ch. 10.SE - Prob. 26APCh. 10.SE - A chemist requires a large amount of...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product would you expect from the reaction of...Ch. 10.SE - Rank the compounds in each of the following series...Ch. 10.SE - Which of the following compounds have the same...Ch. 10.SE - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 34APCh. 10.SE - Alkylbenzenes such as toluene (methylbenzene)...Ch. 10.SE - Prob. 36APCh. 10.SE - Prob. 37APCh. 10.SE - Prob. 38APCh. 10.SE - Prob. 39APCh. 10.SE - Prob. 40APCh. 10.SE - The syntheses shown here are unlikely to occur as...Ch. 10.SE - Why do you suppose its not possible to prepare a...Ch. 10.SE - Prob. 43APCh. 10.SE - Identify the reagents a–c in the following...Ch. 10.SE - Prob. 45APCh. 10.SE - Prob. 46APCh. 10.SE - Prob. 47APCh. 10.SE - The relative rate of radical bromination is...Ch. 10.SE - Prob. 49APCh. 10.SE - Predict the product and provide the entire...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH,CH,CH,CH,CCH, Br b) For the major elimination product obtained in 5a), which stereoisonmer (cis or trans) is obtained in greater yield? Draw the two isomers and provide the names of the compounds.arrow_forward5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH;CH,CH,CH,CCH, Br 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_forwardWhen HBr adds to (CH3)2C = CH2 under radical conditions, two radicals are possible products in the first step of chain propagation. Draw the structure of both radicals and indicate which one is formed. Then draw the preferred product from HBr addition under radical conditions.arrow_forward
- What is the predicted product of the reaction shown? O & N(CH3)2 | IV (CH3)2NH H₂SO4 1. N(CH3)2 2. H3O+ || ОН HO |||arrow_forwardQ2. Consider the nucleophilic substitution reaction between 3-chloro-3-methylpentane and the hydroxide ion: CI x + OH (a) Is the alkyl halide 1°, 2° or 3°? (b) Will the nucleophilic substitution reaction be S₁1 or S№2? (c) Give the substitution mechanism showing all full and partial positive and negative charges, electron movements using curved arrows.arrow_forwardDraw a structural formula for the substitution product of the reaction shown below. ● H3C HH Br + O • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If more than one stereoisomer of product is formed, draw both. Separate multiple products using the + sign from the drop-down menu. • Products that are initially formed as ions should be drawn in their neutral forms. ▼ In [F OCH 3 -85 ? Na CN CH3CH₂OH ChemDoodleⓇ >arrow_forward
- CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, 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 CH,Cl,. 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 CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:arrow_forward4. What are the products obtained from the following elimination reaction? Indicate the major product. CH3 CH,CH,ČCH, H2O 5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH;CH,CH,CH,CCH, Br 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 structure of the alkene with the molecular formula CH10 that reacts with Br, to give this compound. CH3 Br Br • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. opyste ot pt pt pt ptarrow_forward
- 1. Reaction of 2,3-dimethyl-1-butene with HBr leads to an alkyl bromide, C6H13Br. On treatment of this alkyl halide with KOH in methanol, elimination of HBr occurs and a hydrocarbon that is isometric with the starting alkene is formed. What is the structure of this hydrocarbon and how do you think it is formed from an alkyl bromide? 2. 1-Octen-3-ol is a potent mosquito attractant commonly used in mosquito traps. A number of reactions, including hydrogenation, will transform 1-Octen-3-ol into a less effective molecule. Write a complete reaction equation for the hydrogenation of this alkenol.arrow_forwardThe two alkenes below react with HI at different rates. CH3CH=CHCH3 and CH₂=CH₂ Draw the structural formula of the MAJOR product formed by the alkene having the HIGHER reaction rate. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. TAYY [ ] در ChemDoodle Ⓡarrow_forwardDraw structural formulas for the major organic product(s) of the reaction shown below. CN AICI3 + (CH3)2CHCI • You do not have to consider stereochemistry. If no reaction occurs, draw the organic starting material. Remember to include all of the formal charges on the atoms of any nitro groups.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you