Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
5th Edition
ISBN: 9781260170405
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 8, Problem 8.42P
In the dehydrohalogenation of bromocyclodecane, the major product is cis-cyclodecene
rather than trans-cyclodecene. Offer an explanation.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
In the dehydrohalogenation of bromocyclodecane, the major product is cis -cyclodecene rather than trans-cyclodecene. Offer an explanation.
describe about the stability of some compounds ( provide some examples) and intermediates such as double bonds (Zaitsev rule), carbocations, carbanions, and carbenes.
Compounds X and Y are both C5H11CI products formed in the radical chlorination of pentane.
Base-promoted E2 elimination of X and Y gives, in each case, a single C5H10 alkene (ignoring double bond
stereochemistry).
Both X and Y react in SN2 fashion with sodium iodide in acetone; Y reacts faster than X.
What is the structure of Y?
• Do not use stereobonds in your answer.
• In cases where there is more than one possible structure for each molecule, just give one for each.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right
corner.
• Separate structures with + signs from the drop-down menu.
ChemDoodle
(Previous
Next
Chapter 8 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
Ch. 8 - Problem 8.1 Label the and carbons in each alkyl...Ch. 8 - Problem 8.2 Classify each alkene in the following...Ch. 8 - Prob. 8.3PCh. 8 - Prob. 8.4PCh. 8 - Problem 8.5 Label each pair of alkenes as...Ch. 8 - Problem 8.6 Which alkene in each pair is more...Ch. 8 - Problem 8.7 Several factors can affect alkene...Ch. 8 - Prob. 8.8PCh. 8 - Prob. 8.9PCh. 8 - Prob. 8.10P
Ch. 8 - Prob. 8.11PCh. 8 - Problem 8.12 What alkenes are formed from each...Ch. 8 - Prob. 8.13PCh. 8 - Problem 8.14 What alkenes are formed from each...Ch. 8 - Problem 8.15 How does each of the following...Ch. 8 - Problem 8.16 Draw both the SN1 and E1 products of...Ch. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Problem 8.19 Explain why...Ch. 8 - Prob. 8.20PCh. 8 - Problem 8.21 Draw the alkynes formed when each...Ch. 8 - Problem 8.22 Draw the products in each...Ch. 8 - Problem 8.23 Draw a stepwise mechanism for the...Ch. 8 - 8.24 Rank the alkenes shown in the ball-and-stick...Ch. 8 - Prob. 8.25PCh. 8 - 8.26 What is the major E2 elimination product...Ch. 8 - Prob. 8.27PCh. 8 - Prob. 8.28PCh. 8 - Prob. 8.29PCh. 8 - 8.30 Label each pair of alkenes as constitutional...Ch. 8 - Prob. 8.31PCh. 8 - Prob. 8.32PCh. 8 - Prob. 8.33PCh. 8 - For each of the following alkenes, draw the...Ch. 8 - Prob. 8.35PCh. 8 - Prob. 8.36PCh. 8 - Prob. 8.37PCh. 8 - What alkene is the major product formed from each...Ch. 8 - Prob. 8.39PCh. 8 - Prob. 8.40PCh. 8 - Pick the reactant or solvent in each part that...Ch. 8 - 8.42 In the dehydrohalogenation of...Ch. 8 - Prob. 8.43PCh. 8 - Prob. 8.44PCh. 8 - Prob. 8.45PCh. 8 - Prob. 8.46PCh. 8 - Prob. 8.47PCh. 8 - Prob. 8.48PCh. 8 - What alkyl chloride affords the following alkene...Ch. 8 - Draw the products formed when each dihalide is...Ch. 8 - Draw the structure of a dihalide that could be...Ch. 8 - Under certain reaction conditions, 2,...Ch. 8 - For which reaction mechanisms, SN1, SN2, E1 or...Ch. 8 - Draw the organic products formed in each...Ch. 8 - Prob. 8.55PCh. 8 - Draw all products, including stereoisomers, in...Ch. 8 - Draw all of the substitution and elimination...Ch. 8 - Prob. 8.58PCh. 8 - 8.59 Draw a stepwise, detailed mechanism for each...Ch. 8 - Draw the major product formed when...Ch. 8 - Draw a stepwise, detailed mechanism for the...Ch. 8 - Explain why the reaction of with gives ...Ch. 8 - Draw a stepwise detailed mechanism that...Ch. 8 - Prob. 8.64PCh. 8 - 8.65 Explain the selectivity observed in the...Ch. 8 - Prob. 8.66PCh. 8 - Prob. 8.67PCh. 8 - 8.68 (a) Draw all products formed by treatment of...
Additional Science Textbook Solutions
Find more solutions based on key concepts
Practice Problem 1.22 Which of the following alkenes can exist as cis-trans isomers? Write their structures. Bu...
Organic Chemistry
Practice Exercise 1
Which of the following factors determines the size of an atom? a. the volume of the nucleus...
Chemistry: The Central Science (14th Edition)
Give one example from main group chemistry that illustrates each of the following descriptions: (a) Covalent ne...
General Chemistry: Atoms First
Q2. Which statement best defines chemistry?
a. The science that studies solvents, drugs, and insecticides
b. Th...
Introductory Chemistry (6th Edition)
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
- Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibromide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?arrow_forwardDraw the alkene structure that produced the following compounds in a ozonolysis reaction as specified. 1. O3 2. (CH3)2S 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.arrow_forwardReaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis-and trans-1-bromo-3-methylcyclohexane and cis-and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1, 2-dibromocyclohexane as the soleproduct. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.arrow_forward
- A catalytic reduction of an alkene is shown below, what are all the possible products produced from this reaction. What is the relationship between the products? Is this a stereoselective, stereospecific reaction or neither? Explain. H2, Pd/Carrow_forward11.; (a) Similar to alkanes, hydrogen gas can undergo radical bromination according to the reaction below. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46 kcal·mole', for H-Br is 88 kcal'mole and for H-H is 104 kcal'mole'. hv H-H + Br-Br 2 H-Br (b) Calculate the overall AH for the above propagation steps (show all work).arrow_forwardHw.203.arrow_forward
- Electrophilic addition to an alkene proceeds via Markovnikov regiochemistry due to the formation of the more stable carbocation intermediate. In the case of conjugated dienes, that is dienes that are separated by one sigma bond, the carbocation that is formed is stabilized additionally by resonance. Addition of the nucleophile to the carbocation intermediate can therefore give two types of products: direct addition to the double bond, also called 1,2-addition, and conjugate addition to the resonance stabilized carbocation, also called 1,4-addition.Allylic carbocation stability is affected by both the nature of the carbocation (primary allylic, secondary allylic, or tertiary allylic) and by the degree of substitution of the double bond. The latter is typically the dominant effect and so a primary allylic carbocation with a trisubstituted double bond is more stable than a tertiary allylic carbocation with a monosubstituted double bond.Electrophilic addition to a conjugated diene is…arrow_forward[References] Draw the alkene structure that produced the following compounds in a ozonolysis reaction as specified. 1. O3 C7H12 2. (CH3)2Sarrow_forwardTo make Halocyclopentane, what reagents and substartes are needed? Which one(below) is related with the Halocyclopentane? Esterification, Alcohol Halogenation ,Alkyl Halide Solvolysis, Alkene Hydration, Hydroboration, Alkene Bromination, Alkene Dihydroxylation, Epoxidation, Diels Alder, Aldol, Grignard Addition, Benzene Nitration, Friedel-Crafts, Carbonyl Reduction, Claisen Condensation, Alcohol Oxidationarrow_forward
- Review Topics] [References] Draw a structural formula for the major product of the reaction shown. CH;CH2 c=CHCH3 CH;CH2 Br2 H20 • Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. Previous Next ChemDoodle Save and Ex tv ill I 11 МacBook Air DII DD F12 F11 F10 80 888 F9 F7 FB F6 F5 F4 F3 * & $ %3D 5 6. 7 8 9. 4 { P E R T Y H J K F + * COarrow_forward(Z)-3-methyl- pent-2 - ene is reacted with Br2 in CH3OH, as shown in the reaction scheme below.Complete the structure for one stereoisomer for the minor regioisomer formed in this reaction, including stereochemistry where appropriate. Draw both the wedged and dashed bonds at each stereogenic carbon atom.arrow_forwardAs shown in Scheme 4 and in the image below, the exo-cycloadduct is presented in 3-D. Select the correct 2-D depiction of the same molecule. 4¢¢¢¢ C a Select an answer and submit. For keyboard navigation, use the up/down arrow keys to select an answer. b B C A e C d D A E exo-product B D Earrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY