Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 7.SE, Problem 69AP
Interpretation Introduction
Interpretation:
An energy diagram for the addition of HBr to 1-pentene is to be drawn. Both the curves, one for the formation of 1-bromopentane and another for the formation of 2-bromopentane, are to be shown in the same diagram indicating the positions of all the reactants, intermediates and products.The curve which has the higher-energy carbocation intermediate and that which has the higher-energy first transition state are to be identified.
Concept introduction:
The carbocation II is more stable than I. Hence it is easily formed, has less energy and its formation will be more exergonic.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
What about the second step in the electrophilic addition of HCl to an alkene-the reaction of chloride ion with the carbocation intermediate? Is this step exergonic or endergonic? Does the transition state for this second step resemble the reactant (carbocation) or the product (alkyl chloride)? Make a rough diagram of what the transition state may look like?
Draw eugenol as a line structure. The double bonds of the benzene ring are fairly unreactive unless you use special catalysts. But the double bond on the side group is reactive. Draw the mechanism of eugenol reacting with HBr to form the two possible carbocation intermediates. Put your intermediates into square brackets. Label each carbocation as a methyl carbon or 1°, 2°, or 3°. Then circle a more stable carbocation if one is more stable. Can you guess what the final product is?
The pictured reaction shows an alkyl bromide being converted into an alkene.
Choose all reagents that would produce the pictured alkene as the major product.
A) NaOH/H2O
B) H2O
C) tBuOK/tBuOH
D) EtONa/EtOH
Chapter 7 Solutions
Organic Chemistry
Ch. 7.2 - Calculate the degree of unsaturation in each of...Ch. 7.2 - Prob. 2PCh. 7.2 - Diazepam, marketed as an antianxiety medication...Ch. 7.3 - Give IUPAC names for the following compounds:Ch. 7.3 - Prob. 5PCh. 7.3 - Prob. 6PCh. 7.3 - Prob. 7PCh. 7.4 - Prob. 8PCh. 7.4 - Prob. 9PCh. 7.4 - Prob. 10P
Ch. 7.5 - Which member in each of the following sets ranks...Ch. 7.5 - Prob. 12PCh. 7.5 - Prob. 13PCh. 7.5 - Prob. 14PCh. 7.6 - Prob. 15PCh. 7.8 - Prob. 16PCh. 7.8 - Prob. 17PCh. 7.9 - Show the structures of the carbocation...Ch. 7.9 - Draw a skeletal structure of the following...Ch. 7.10 - Prob. 20PCh. 7.11 - On treatment with HBr, vinylcyclohexane undergoes...Ch. 7.SE - Prob. 22VCCh. 7.SE - Prob. 23VCCh. 7.SE - The following carbocation is an intermediate in...Ch. 7.SE - Prob. 25VCCh. 7.SE - Predict the major product and show the complete...Ch. 7.SE - Prob. 27MPCh. 7.SE - When 1, 3-butadiene reacts with one mole of HBr,...Ch. 7.SE - When methyl vinyl ether reacts with a strong acid,...Ch. 7.SE - Addition of HCl to 1-isopropylcyclohexene yields a...Ch. 7.SE - Addition of HCl to...Ch. 7.SE - Limonene, a fragrant hydrocarbon found in lemons...Ch. 7.SE - Prob. 33MPCh. 7.SE - Calculate the degree of unsaturation in the...Ch. 7.SE - Prob. 35APCh. 7.SE - Prob. 36APCh. 7.SE - Name the following alkenes:Ch. 7.SE - Draw structures corresponding to the following...Ch. 7.SE - Prob. 39APCh. 7.SE - Prob. 40APCh. 7.SE - Prob. 41APCh. 7.SE - Prob. 42APCh. 7.SE - Prob. 43APCh. 7.SE - Draw and name the 17 alkene isomers, C6H12,...Ch. 7.SE - Prob. 45APCh. 7.SE - Prob. 46APCh. 7.SE - Which of the following E, Z designations are...Ch. 7.SE - Prob. 48APCh. 7.SE - trans-2-Butene is more stable than cis-2-butene by...Ch. 7.SE - Prob. 50APCh. 7.SE - Normally, a trans alkene is more stable than its...Ch. 7.SE - trans-Cyclooctene is less stable than...Ch. 7.SE - Prob. 53APCh. 7.SE - Prob. 54APCh. 7.SE - Use Hammond’s Postulate to determine which...Ch. 7.SE - Prob. 56APCh. 7.SE - Predict the major product in each of the following...Ch. 7.SE - Prob. 58APCh. 7.SE - Prob. 59APCh. 7.SE - Prob. 60APCh. 7.SE - Allene (1,2-propadiene), H2C=C=CH2, has two...Ch. 7.SE - The heat of hydrogenation for allene (Problem...Ch. 7.SE - Retin A, or retinoic acid, is a medication...Ch. 7.SE - Prob. 64APCh. 7.SE - tert-Butyl esters [RC02C(CH3)3] are converted into...Ch. 7.SE - Vinylcyclopropane reacts with HBr to yield a...Ch. 7.SE - Prob. 67APCh. 7.SE - Prob. 68APCh. 7.SE - Prob. 69APCh. 7.SE - Prob. 70APCh. 7.SE - Prob. 71APCh. 7.SE - Reaction of 2, 3-dimethyl-l-butene with HBr leads...
Knowledge Booster
Similar questions
- draw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocationarrow_forwardFor each rate equation, what effect does the indicated concentration change have on the overall rate of the reaction?[1] rate = k[CH3CH2Br][-OH]a. tripling the concentration of CH3CH2Br onlyb. tripling the concentration of -OH onlyc. tripling the concentration of both CH3CH2Br and -OH[2] rate = k[(CH3)3COH]a. doubling the concentration of (CH3)3COHb. increasing the concentration of (CH3)3COH by a factor of 10arrow_forwardorganic chemistry help Fill in the missing starting materials, reagents, or major products of each reactionarrow_forward
- Fill in any starting materials, reagents, or products to complete the reaction.arrow_forwardWhat is the intermediate before the final product of the following reactions?arrow_forwardWhat happens in the rate-limiting step of the reaction? a) The bromide ion detaches from the alkyl halide and a carbocation intermediate is formed b) Ethanol attacks the alkyl halide carbon and replaces the leaving group c) The speed-limiting step is unknown d) Ethanol is associated with a carbocationarrow_forward
- Draw an energy diagram for the addition of hydrobromic acid to pent-1-ene. Two products formin this reaction; draw the curves for both. Label the positions of the reactions, intermediates,and products. What is the name of the product that forms from the curve that has the higher-energy carbocation intermediate? What is the name of the product that forms from the curvethat has the higher-energy first transition state?The product of both the higher-energy carbocation intermediate and higher-energy first transitionstate is 1-bromopentane.arrow_forwardFinish ONE of the indicated reactions by filling in any starting materials, reagents, or products as needed.arrow_forwardlist the reagents that are needed to carry out in these reactionsarrow_forward
- Addition of HCl to alkene X forms two alkyl halides Y and Z. Label Y and Z as a 1,2-addition product or a 1,4-addition productarrow_forwardOrganic Chemistry Indicate which carbocation is the most stable carbocation and which carbocation is the least stable carbocation?Çok Satırlı Metin.arrow_forwardWhat are the reagents and intermediates to get to this productarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning