Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 4, Problem 51P
Interpretation Introduction
Interpretation:The structure of cyclodecane in a chair conformation needs to be compared with trans-decalin. The reason for all the chair conformationz to be highly strained and trans decalin to be strain free needs to be explained.
Concept introduction:The strain in the molecule is due to a change in the C-C-C bond angle. In cyclohexane, carbon atom undergoes sp3 hybridization and the expected bond angle is 109.5o.
The formula to calculate bond angle in cyclic structure is,
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The compounds drawn should each contain a cyclohexane ring. For all three compounds draw a wedge and dash structure, Chair I, and Chair II conformations.
Formula: C9H18 with substitution 1,1- disubstituted with stereochemistry of (R,S)
Formula: C7H13Cl with substitution 1,3- disubstituted with stereochemistry of (R,R)
Formula: C7H14O with substitution 1,4- disubstituted with stereochemistry (S,S)
2. Draw the two chair conformations of 3-tert-utyl-1-methylcyclohexanol and estimate the amount of strain
energy in each. Which conformation is favored?
2) Draw Newman projections of all staggered conformations of (S)-butan-2-ol. Clearly mark the
highest energy conformation.
3) Draw both chair conformations of (1S,3R)-1-chloro-3-isopropylcyclohexane. Clearly mark the
most stable conformation, and also the conformation which enables E2 elimination.
Chapter 4 Solutions
Organic Chemistry: Structure and Function
Ch. 4.1 - Prob. 4.1ECh. 4.1 - Prob. 4.3TIYCh. 4.2 - Prob. 4.4ECh. 4.2 - Prob. 4.6TIYCh. 4.3 - Prob. 4.7ECh. 4.4 - Prob. 4.8ECh. 4.4 - Prob. 4.10TIYCh. 4.4 - Prob. 4.11ECh. 4.4 - Prob. 4.12ECh. 4.4 - Prob. 4.14TIY
Ch. 4.6 - Prob. 4.15ECh. 4.7 - Prob. 4.16ECh. 4.7 - Prob. 4.17ECh. 4.7 - Prob. 4.18ECh. 4 - Prob. 21PCh. 4 - Prob. 22PCh. 4 - Prob. 23PCh. 4 - Prob. 24PCh. 4 - Prob. 25PCh. 4 - Prob. 26PCh. 4 - Prob. 27PCh. 4 - Prob. 28PCh. 4 - Prob. 29PCh. 4 - Prob. 30PCh. 4 - Prob. 31PCh. 4 - Prob. 32PCh. 4 - Prob. 33PCh. 4 - Prob. 34PCh. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - Prob. 37PCh. 4 - Prob. 38PCh. 4 - Prob. 39PCh. 4 - Prob. 40PCh. 4 - Prob. 41PCh. 4 - Prob. 42PCh. 4 - Prob. 43PCh. 4 - Prob. 44PCh. 4 - Prob. 45PCh. 4 - Prob. 46PCh. 4 - Prob. 47PCh. 4 - Prob. 48PCh. 4 - Prob. 49PCh. 4 - Prob. 50PCh. 4 - Prob. 51PCh. 4 - Prob. 52PCh. 4 - Prob. 53PCh. 4 - Prob. 54PCh. 4 - Prob. 55PCh. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Prob. 59PCh. 4 - Prob. 60P
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
- Draw the structures for (Z)-3-methylhex-3-ene and the two major organic products for its reaction with HBr. Be sure to show all stereoisomers using wedge and dash stereochemistry at any chirality center.arrow_forwardTrans-1-bromo-2-methylcyclohexane will yield a non-Zaitsev elimination product (3-methylcyclohexene) upon reaction with KOH. Show this reaction by drawing the chair conformations of the reactant and product. Include the curved arrows and explain why the product is not a non-Zaitsev product.arrow_forward11. Trans-1-bromo-2-methylcyclohexane will yield a non-Zaitsev elimination product (3- methylcyclohexene) upon reaction with KOH. Show this reaction by drawing the chair conformations of the reactant and product. Include the curved arrows and explain why the product is not a non-Zaitsev product. (arrow_forward
- Draw all possible conformations of trans-1,3-dichlorocyclobutane. Which of the conformation of trans-1,3-dichlorocyclobutane is the most stable? Explain your answer.arrow_forwardFrom trans-1-chloro-2-isopropylcyclohexane, only 3-isopropylcyclohexene, the less substituted alkene, is formed. Using conformational analysis, explain why this product is observed. Also, will the E2 reaction with trans-1-chloro- 2-isopropylcyclohexane or cis-1-chloro-2-isopropylcyclohexane occur faster under the same basic conditions? CH;O Na* CH3OH CI trans-1-Chloro-2 (R)-3-Isopropylcyclohexene isopropylcyclohexanearrow_forward(a) Draw all stereoisomers formed by monochlorination of the cis and trans isomers of 1,2-dimethylcyclobutane drawn below. (b) How many constitutional isomers are formed in each reaction? (c) Label any pairs of enantiomers formed.arrow_forward
- Define the degree of unsaturation ?arrow_forwardDraw the highest and lowest energy conformations. In cases where two or three conformations are degenrate, choose only one as your answer. Use Ch2Ch3, H and Ch3 for the structure.arrow_forwardWe saw that the energy cost of an axial methyl is 1.8 kcal/mol; therefore, we might expect cis-1,3-dimethylcyclohexane to have chair conformations with a difference in totalenergy of 3.6 kcal/mol. 1. Is the calculated energy difference in cis-1,3-dimethylcyclohexane higher or lower than expected? Propose an explanation for the difference between the expected energy difference and the calculated energy difference in cis-1,3-dimethylcyclohexane. (Limit your answer to 10 words or fewer) 2. Recall that an axial methyl is typically worth around 1.8 kcal/mol. Propose an explanation for the difference in the value above for 1-methyltetrahydropyran. (Limit your answer to 10 words or less) 3. Would you expect the difference in strain energy between the chairs of 5-methyl-1,3-dioxane to be greater than or less than that of 1-methyltetrahydropyran? Is it GREATER THAN or LESS THAN?arrow_forward
- Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.arrow_forwardFollowing is a planar hexagon representation of L-fucose, a sugar component of the determinants of the A, B, O blood group typing. For more on this system of blood typing, see Chemical Connections: A, B, AB, and O Blood Group Substances in Chapter 25. (a) Draw the alternative chair conformations of L-fucose. (b) Which of them is more stable? Explain.arrow_forwardThe following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy conformation of the molecule. Why are the two benzene rings tilted at a 63� angle to each other rather than being in the same plane so that their p orbitals overlap? Why doesn't complete rotation around the single bond joining the two rings occur?arrow_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: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning