
Interpretation:
The possible products resulting from the addition of one equivalent of HCl to 1-phenyl-1,3-butadiene are to be given. Which product predominates is to be stated and the reason for the same also is to be given.
Concept introduction:
Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of bromide ion on each of these forms leads to the formation of a mixture of 1,2- and 1,4-addition products. The more stable allylcation produced will yield the major product.
To give:
The possible products resulting from the addition of one equivalent of HCl to 1-phenyl-1,3-butadiene.
To state:
Which product predominates and to give the reason for the same.

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Chapter 14 Solutions
Organic Chemistry - With Access (Custom)
- Q1: Answer the questions for the reaction below: ..!! Br OH a) Predict the product(s) of the reaction. b) Is the substrate optically active? Are the product(s) optically active as a mix? c) Draw the curved arrow mechanism for the reaction. d) What happens to the SN1 reaction rate in each of these instances: 1. Change the substrate to Br "CI 2. Change the substrate to 3. Change the solvent from 100% CH3CH2OH to 10% CH3CH2OH + 90% DMF 4. Increase the substrate concentration by 3-fold.arrow_forwardExperiment 27 hates & Mechanisms of Reations Method I visual Clock Reaction A. Concentration effects on reaction Rates Iodine Run [I] mol/L [S₂082] | Time mo/L (SCC) 0.04 54.7 Log 1/ Time Temp Log [ ] 13,20] (time) / [I] 199 20.06 23.0 30.04 0.04 0.04 80.0 22.8 45 40.02 0.04 79.0 21.6 50.08 0.03 51.0 22.4 60-080-02 95.0 23.4 7 0.08 0-01 1970 23.4 8 0.08 0.04 16.1 22.6arrow_forward(15 pts) Consider the molecule B2H6. Generate a molecular orbital diagram but this time using a different approach that draws on your knowledge and ability to put concepts together. First use VSEPR or some other method to make sure you know the ground state structure of the molecule. Next, generate an MO diagram for BH2. Sketch the highest occupied and lowest unoccupied MOs of the BH2 fragment. These are called frontier orbitals. Now use these frontier orbitals as your basis set for producing LGO's for B2H6. Since the BH2 frontier orbitals become the LGOS, you will have to think about what is in the middle of the molecule and treat its basis as well. Do you arrive at the same qualitative MO diagram as is discussed in the book? Sketch the new highest occupied and lowest unoccupied MOs for the molecule (B2H6).arrow_forward
- Q8: Propose an efficient synthesis of cyclopentene from cyclopentane.arrow_forwardQ7: Use compound A-D, design two different ways to synthesize E. Which way is preferred? Please explain. CH3I ONa NaOCH 3 A B C D E OCH3arrow_forwardPredict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2).arrow_forward
- (10 pts) The density of metallic copper is 8.92 g cm³. The structure of this metal is cubic close-packed. What is the atomic radius of copper in copper metal?arrow_forwardPredict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2).arrow_forwardPredict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2).arrow_forward
- Q3: Rank the following compounds in increasing reactivity of E1 and E2 eliminations, respectively. Br ca. go do A CI CI B C CI Darrow_forwardQ5: Predict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2). H₂O דיי "Br KN3 CH3CH2OH NaNH2 NH3 Page 3 of 6 Chem 0310 Organic Chemistry 1 HW Problem Sets CI Br excess NaOCH 3 CH3OH Br KOC(CH3)3 DuckDuckGarrow_forwardQ4: Circle the substrate that gives a single alkene product in a E2 elimination. CI CI Br Brarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
