Pushing Electrons
4th Edition
ISBN: 9781133951889
Author: Weeks, Daniel P.
Publisher: Cengage Learning
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Textbook Question
Chapter 1, Problem 76EQ
Heterolytic cleavage of the
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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:
All electrophilic aromatic substitution reactions occur via a two-step mechanism: addition of the electrophile to form a resonance-stabilized carbocation, followed
by deprotonation by a base.
In the step shown below, loss of a proton to form the substitution product was drawn using the resonance structure with the + 1 formal charge at the ortho
position to the carbon bonded to the electrophile. Redraw the step shown with the other two resonance structures and use curved arrows to show how these
other two resonance structures can be converted to the substitution product by removal of a proton with the base shown.
Part: 0/2
Part 1 of 2
H
:CI-AICI,
Draw the mechanism that generates the final substitution product with the +1 formal charge at the para position.
Cl
HC1
AICI3
how H2O2 can be prepared on the large scale?
Chapter 1 Solutions
Pushing Electrons
Ch. 1 - 1. Hydrogen is a Group I element and each...Ch. 1 - Methanol has the molecular formula CH4O. Its...Ch. 1 - 3. The skeleton of chloromethane is...Ch. 1 - 4. Methanol’s skeleton is
Connecting all bonded...Ch. 1 - 5. The structure for chloromethane is
It...Ch. 1 - Prob. 6EQCh. 1 - 7. Dimethyl ether
No. of electrons in...Ch. 1 - Methylamine (CH5N) No. of electrons in structure...Ch. 1 - Methanethiol (CH4S) No. of electrons in structure...Ch. 1 - Methylal (C3H8O2) No. of electrons in structure...
Ch. 1 - Prob. 11EQCh. 1 - Adding electrons to the skeleton by making single...Ch. 1 - This is done by removing an unshared pair from...Ch. 1 - Prob. 14EQCh. 1 - Prob. 15EQCh. 1 - Prob. 16EQCh. 1 - The skeleton of acetyl chloride is . Write the...Ch. 1 - Three constitutional isomers exist for the formula...Ch. 1 - A number of constitutional isomers exist for the...Ch. 1 - Using the method outlined above, derive the...Ch. 1 - Prob. 21EQCh. 1 - Prob. 22EQCh. 1 - Prob. 23EQCh. 1 - Prob. 24EQCh. 1 - The skeleton of benzyldimethylamine is
The...Ch. 1 - The skeleton is benzaldoxime is The number of...Ch. 1 - Prob. 27EQCh. 1 - Derive Lewis structures for the compounds below....Ch. 1 - Prob. 29EQCh. 1 - Derive Lewis structures for the compounds below....Ch. 1 - Prob. 31EQCh. 1 - Derive Lewis structures for the compounds below....Ch. 1 - The Lewis structure of acetone is Circling the...Ch. 1 - Chloromethane has the Lewis...Ch. 1 - In the Lewis structure for chloromethane, the...Ch. 1 - Prob. 36EQCh. 1 - The oxygen atom in acetone possesses ____ unshared...Ch. 1 - Nitrobenzene has the skeleton
The number of...Ch. 1 - Prob. 39EQCh. 1 - Compute and add on the formal charges I these...Ch. 1 - Prob. 41EQCh. 1 - Prob. 42EQCh. 1 - Prob. 43EQCh. 1 - Prob. 44EQCh. 1 - Prob. 45EQCh. 1 - Prob. 46EQCh. 1 - Prob. 47EQCh. 1 - Compute and add on the formal charges in these...Ch. 1 - Prob. 49EQCh. 1 - Prob. 50EQCh. 1 - The n-propyl cation can be formed from a molecule...Ch. 1 - Prob. 52EQCh. 1 - Prob. 53EQCh. 1 - Methanol, CH3OH, is a compound in which the formal...Ch. 1 - When a proton becomes bonded to diethyl ether, by...Ch. 1 - Tetrahydrofuran has the structure
When a proton...Ch. 1 - Prob. 57EQCh. 1 - Prob. 58EQCh. 1 - The structure of pyridine is
When a proton...Ch. 1 - The carbon atom owns one electron from each of ...Ch. 1 - The n-butyl anion can be formed from When the CLi...Ch. 1 - The isobutyl anion can be formed from When the CNa...Ch. 1 - Prob. 63EQCh. 1 - Ethanol, , is a compound in which the formal...Ch. 1 - The loss of a proton attached to the oxygen atom...Ch. 1 - A very strong base can remove a proton from...Ch. 1 - Prob. 67EQCh. 1 - Prob. 68EQCh. 1 - Prob. 69EQCh. 1 - The homolysis of the OO bond in diacetyl peroxide...Ch. 1 - Prob. 71EQCh. 1 - Prob. 72EQCh. 1 - Prob. 73EQCh. 1 - Prob. 74EQCh. 1 - Prob. 75EQCh. 1 - Heterolytic cleavage of the CO bond to yield a...Ch. 1 - Prob. 77EQCh. 1 - Prob. 78EQCh. 1 - Prob. 79EQCh. 1 - Prob. 80EQ
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- Shown below is a carbocation intermediate in an electrophilic addition reaction of HCl with an alkene. For the conformation shown, select each hydrogen whose bond to carbon is aligned for effective hyperconjugation with the vacant p orbital on the positively charged carbon. Each adjacent carbon will have only one C-H bond so aligned. • Gray = C; white = H; red = 0; blue = N; dark green = Cl; brown =Br; light green =F; purple = I; yellow = S; orange = P. • Double click to select atoms. • You can zoom in and out using the mouse scroll wheel (or pinch to zoom on touch screens).arrow_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_forwardFor the substitution reaction. Draw the structure of the intermediate that forms in the rate determining step. Он HBr (aq) Brarrow_forward
- Desribe the reaction product.arrow_forwardWhich 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 + ·CH3arrow_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_forward
- Define the Mechanism of the Radical Addition of HBr to an Alkene ?arrow_forward2. The following carbocation is generated as an intermediate in the addition of H-Br to an alkene. Draw the structure of all possible alkenes that could have formed this intermediate.arrow_forwardThe first step of the addition of a hydrogen halide to an alkene is the addition of H+ to an sp2 carbon to form a carbocation. Predict the carbocation formed in the following reaction and draw the mechanism of its formation. Edit the reaction by drawing all steps in the appropriate boxes and connecting them with reaction arrows. Add charges where needed. Electron-flow arrows should start on an atom or a bond and should end on an atom, bond, or location where a new bond should be created.arrow_forward
- The first step of the addition of a hydrogen halide to an alkene is the addition of H+ to an sp² carbon to form a carbocation. Predict the carbocation formed in the following reaction and draw the mechanism of its formation. Edit the reaction by drawing all steps in the appropriate boxes and connecting them with reaction arrows. Add charges where needed. Electron-flow arrows should start on an atom or a bond and should end on an atom, bond, or location where a new bond should be created. + CeH= H₂C H- -Br: H₂C H с N O S CI Br P Farrow_forwardThe first step of the addition of a hydrogen halide to an alkene is the addition of H+ to an sp² carbon to form a carbocation. Predict the carbocation formed in the following reaction and draw the mechanism of its formation. Edit the reaction by drawing all steps in the appropriate boxes and connecting them with reaction arrows. Add charges where needed. Electron-flow arrows should start on an atom or a bond and should end on an atom, bond, or location where a new bond should be created. 4²² 0 0 0 1² ²0 +²²E NN H₂C -CH₂ H EXP CONT H-Br: H C N O S CI Br I Parrow_forwardThe first step of the addition of a hydrogen halide to an alkene is the addition of H+ to an sp² carbon to form a carbocation. Predict the carbocation formed in the following reaction and draw the mechanism of its formation. Edit the reaction by drawing all steps in the appropriate boxes and connecting them with reaction arrows. Add charges where needed. Electron-flow arrows should start on an atom or a bond and should end on an atom, bond, or location where a new bond should be created. □ C MN + T [1] A H₂C -CH₂ 7 L H EXP. CONT. i ? L H-Br: Ø H с N O S CI Br I P Farrow_forward
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