Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Question
Chapter 9.7, Problem 30P
Interpretation Introduction
Interpretation:
Acetate ion will be a better nucleophile in dimethyl sulfoxide or methanol in an SN2 reaction is to be identified.
Concept Introduction:
The SN2/E2 reaction of
An SN2 reaction of an alkyl halide is favoured by a high concentration of a good (negatively charged) nucleophile in an
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
What is the nucleophile in the following reaction?
2H2
0 + CH3! → CH3OH +F + H3O*
12
O CH3I
O CH3OH
O H3O*
5. Which one of the following ions/molecule is the strongest nucleophile?
CH
-SH
A
В
E
Identify the stronger nucleophile in the following pair ?
NH3, −NH2
Chapter 9 Solutions
Organic Chemistry
Ch. 9.1 - Prob. 3PCh. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.2 - Prob. 8PCh. 9.2 - Prob. 9PCh. 9.2 - Prob. 10PCh. 9.2 - Prob. 11PCh. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 14PCh. 9.2 - Prob. 16P
Ch. 9.3 - Prob. 17PCh. 9.4 - Prob. 18PCh. 9.5 - Prob. 19PCh. 9.5 - Prob. 20PCh. 9.5 - Prob. 21PCh. 9.5 - Prob. 22PCh. 9.6 - Prob. 23PCh. 9.6 - Prob. 24PCh. 9.6 - Which of the following reactions take place more...Ch. 9.7 - Prob. 26PCh. 9.7 - Prob. 27PCh. 9.7 - Prob. 28PCh. 9.7 - Prob. 30PCh. 9.7 - Under which of the following reaction conditions...Ch. 9.8 - After a proton is removed from the OH group, which...Ch. 9.8 - Prob. 33PCh. 9.9 - Prob. 34PCh. 9 - Prob. 1PCh. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Prob. 37PCh. 9 - Prob. 38PCh. 9 - Prob. 39PCh. 9 - Prob. 40PCh. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 42PCh. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 44PCh. 9 - Prob. 45PCh. 9 - Prob. 46PCh. 9 - Prob. 47PCh. 9 - Prob. 48PCh. 9 - Prob. 49PCh. 9 - Prob. 50PCh. 9 - Prob. 51PCh. 9 - tert-Butyl chloride undergoes solvolysis in both...Ch. 9 - Prob. 53PCh. 9 - Prob. 54PCh. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 56PCh. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 58PCh. 9 - Prob. 59PCh. 9 - Prob. 60PCh. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 62PCh. 9 - Prob. 63PCh. 9 - Prob. 64PCh. 9 - Prob. 65PCh. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 67PCh. 9 - The reaction of chloromethane with hydroxide ion...
Knowledge Booster
Similar questions
- How does changing the base from −OH to H2O affect the rate of an E2 reaction?arrow_forwardIdentify the best reagent to perform the transformation. CH₂CH₂CH₂OH →→ CH₂CH₂CH₂CH₂ Identify the best reagent. OCH, OH, acetone () 1) NaBr 2) NaOCH, ( CHI O 1) PBr3 2) NaOCH,arrow_forwardGive a reasonable mechanism for this reaction. Explain why it is exothermic. H+ хо Дон H2Oarrow_forward
- Choose the nucleophile best suited for the conversion of an acid chloride to a carboxylic acid. na NaOCH3 CH3NH2 H₂O CH3OH ? OHarrow_forwardFor the following reaction sequence, two of the proposed steps are invalid. (a) Circle the invalid reagents or products, and (b) explain why the step is invalid. NO2 1. HСІ, Fe NH2 NH2 Br2 FeBr3 2. NaOH Br NANO2 HCI NH2 CN N2 NaBH4 CUCN H20 Br Br Brarrow_forwardThe behavior of esters and ketones in a reaction with a nucleophile is different because: 1) the carbonyl of the ketone is more positive. 2) the ester cannot form a tetrahedral intermediate. 3) the two oxygens of the ester sterically hinder the nucleophile attack. 4) there is a reasonable leaving group in the ester. O 2 O 4 O 1arrow_forward
- Which alkyl halide would be unreactive in a nucleophilic substitution reaction? Br I OI O II O III O IV OV Br IV Br II Br V Br IIIarrow_forwardOrganic solvents like benzene, ether, and chloroform are neither protic nor strongly polar. What effect would you expect these solvents to have on the reactivity of a nucleophile in SN2 reaction?arrow_forwardConstruct a three‑step synthesis of 1,2‑epoxycyclopentane from bromocyclopentane by dragging the appropriate formulas into the bins. Note that each bin should hold only one item, and not all of the given reagents or structures will be used. Reactant −→−−−−reagent 1 →reagent 1 Step 1 product −→−−−−reagent 2 →reagent 2 Step 2 product −→−−−−reagent 3 →reagent 3 Final productarrow_forward
- Which of the following statements about the rate of an Sn1 reaction of an alkyl halide is not true? O It is dependent on the structure of the alkyl halide. O All of these are true. O It is dependent on the value of the rate constant. O It is dependent on the concentration of the nucleophile. O It is dependent on the identity of the leaving group.arrow_forwardDecide which compounds from the list below are best suited for nucleophilic addition reactions and which ones are more appropriate for nucleophilic substitution reactions.arrow_forwardSelect the reagent that you would use to convert an alkene to an epoxide. mCPBA 03, then DMS BH3-THF, then H2O2, H2O, NaOH Hg(OAc)2, H2O, then NaBH4arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT