Consider the three structures. 1,1-dimethylcyclobutane (a) Which of these structures has the most angle strain? 1,1-dimethylcyclobutane 1,1,3,3,5,5-hexamethylcyclohexane 1,1,3,3,5,5-hexamethylcyclohexane staggered butane (c) Which of these structures has the most torsional (eclipsing) strain? 1,1,3,3,5,5-hexamethylcyclohexane 1,1-dimethylcyclobutane staggered butane staggered butane H HI H3C staggered butane H H (b) Which of these structures has the most steric strain? 1,1-dimethylcyclobutane CH3 1,1,3,3,5,5-hexamethylcyclohexane

Consider the three structures. 1,1-dimethylcyclobutane (a) Which of these structures has the most angle strain? 1,1-dimethylcyclobutane 1,1,3,3,5,5-hexamethylcyclohexane 1,1,3,3,5,5-hexamethylcyclohexane staggered butane (c) Which of these structures has the most torsional (eclipsing) strain? 1,1,3,3,5,5-hexamethylcyclohexane 1,1-dimethylcyclobutane staggered butane staggered butane H HI H3C staggered butane H H (b) Which of these structures has the most steric strain? 1,1-dimethylcyclobutane CH3 1,1,3,3,5,5-hexamethylcyclohexane

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter2: Alkanes And Cycloalkanes

Section: Chapter Questions

Problem 2.49P: Use your answers from Problem 2.48 to complete the table showing correlations between cis,trans and...

See similar textbooks

Related questions

Q: H "CO2H a.) Group a is Group b is Group c is, H CH3 b.) Group a is Group b is Group c is c.) Group a…

Q: Draw the structure(s) of the cycloalkanes with molecular formula C,H12 that have a 3-membered ring…

A: The molecular formula of the given compound is C6H12. The hydrogen deficiency index for this…

Q: Give the IUPAC name for the following compound:

Q: When cyclohexane is substituted by an ethynyl group, -C=CH, the energy difference between axial and…

Q: The chair conformer of fluorocyclohexane is 0.25 kcal/mol more stable when the fluoro substituent is…

A: Compounds having same molecular formula and different spatial arrangement are called stereoisomers.…

Q: Look at the diagram below and then please answer the following questions: 1) What is the name of the…

A: There are four conformations are used for represent the 6 atm ring

Q: Both cis and trans isomers are possible for which of the following molecules? O cyclobutane…

Q: Give the IUPAC name for the following compound:

A: The rules for writing IUPAC nomenclature for organic compounds are as follows: 1) Select the parent…

Q: DE) 2-methyl-3-ethylhexane hich of the following is not a constitutional isomer of CH3CH2COOH OA)…

Q: Draw the skeletal (line-bond) structure of (1R,2S)-1-bromo-2-methylcyclohexane

A: The given compound is (1R,2S)-1-bromo-2methylcyclohexane.

Q: Make a model of each compound, draw it in its most symmetric conformation, and determine whether it…

A: Asymmetric centre – Asymmetric centre is a molecule having a special arrangement of atoms which is…

Q: Calculate strain energy for the conformer pictured below, using strain energy increments from the…

Q: When (1-bromoethyl)cyclopentane is heated in water for an extended period of time, SIX products…

A: When (1-bromoethyl)cyclopentane is heated in water for an extended period of time, SIX products…

Q: Which of the following is a correct IUPAC name for the molecule shown. CH H,C H. CH,CH,CH2 CH,

A: E stands for Entigen Z stands for Zusament If highest priority atoms or molecules are on same side…

Q: 1. The energy barrier for carbon-carbon bond rotation in propane is mainly due to 2. Which of the…

A: Propane is represented in Newman's projection as shown in figure(1).

Q: CH3 Si. H3C- CH3 Tetramethylsilane (TMS) H3C

Q: Consider a Newman projection of propane shown. Calculate the energy from the strain present in this…

A: An eclipsed conformation is the conformation in which two substituent of two adjacent atoms are in…

Q: Draw a structural formula for 2,4-dimethylpentane.

A: 1. IUPAC's name consists of three parts. 2. prefix+wordroot+suffix prefix again classified into…

Q: 10. Which of the following compounds is 2-methyl-3-(1-methylethyl)hexane? CH3 CH₂-CH-CH-CH₂-CH₂-CH₂…

A: The basic skeleton of iupac nomenclature is " Prefix + Parent + suffix" Parent - the longest carbon…

Q: In which of the following cyclic structures are the bonds in the ring 1.5 X the length of a…

Q: Using Newman projections and an energy diagram, draw all of the conformers of 1,1,2- tribromoethane…

A: The structure of 1,1,2-tribromoethane is:

Q: what kind of isomers are the following pairs (S)-5-Chloro-2-hexene and chlorocyclohexene…

A: The isomers that differ in connectivity are defined as constitutional isomers. The isomers that show…

Q: Why is a substituted cyclohexane ring more stable with a larger group in the equatorial position?

A: Position of substituents in cyclohexane In the conformational analysis cyclohexanes, cis and trans…

Q: The most stable conformer of trans-1-isopropyl-4- methylcyclohexane? Select one: CH3 CH3 CH3

A: To answer this question we have to take care of the interaction it may have. Especially 1,3-diaxial…

Q: 5. Assume that the types of strain in the rotation about the C1-C2 bond in 1,2-dibromopropane have…

A: Structure of 1,2-dibromopropane is:

Q: It is easy to imagine a cyclohexane as a flat hexagon and a lot of the time we draw it that way.…

A: The stability of molecules containing a cyclohexane ring can not be explained by the 2-D structure…

Q: Arrange the following compounds in order of increasing boiling point: H2 (a) .CH3 .CH3 `NH2 CH N. I…

Q: Starting from the wedge-and-dash structure below, rotate the back carbon to provide the Newman…

A: It is an eclipsed conformation in which the largest group of one carbon eclipses the largest group…

Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

Consider the three structures.
1,1-dimethylcyclobutane
1,1,3,3,5,5-hexamethylcyclohexane
(a) Which of these structures has the most angle strain?
O 1,1-dimethylcyclobutane
O 1,1,3,3,5,5-hexamethylcyclohexane
staggered butane
(c) Which of these structures has the most torsional
(eclipsing) strain?
O 1,1,3,3,5,5-hexamethylcyclohexane
O 1,1-dimethylcyclobutane
staggered butane
staggered butane
H
HI
H3C
staggered butane
H
(b) Which of these structures has the most steric strain?
CH3
O 1,1-dimethylcyclobutane
1,1,3,3,5,5-hexamethylcyclohexane

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 2 images

SEE SOLUTION Check out a sample Q&A here

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

Ill Consider the three structures. 1,1,3,3,5,5-hexamethylcyclohexane staggered butane 1,1-dimethylcyclobutane H. CH3 (a) Which of these structures has the most angle strain? (b) Which of these structures has the most steric strain? O 1,1-dimethylcyclobutane O 1,1,3,3,5,5-hexamethylcyclohexane O staggered butane O 1,1-dimethylcyclobutane O 1,1,3,3,5,5-hexamethylcyclohexane O staggered butane (c) Which of these structures has the most torsional MacBook Air 000 000 F7 F5 F8 F10 % 8 } K. 7. B. W
11. s) Draw the most stable conformation of 1,3-dichloro-2,4-difluorocyclohexane: 12. Which of the following represents the most stable conformation of 1,2,4,5- tetramethyleyclohexane? (one correct answer) CH b) CH HC H- H- CH HC CH, CH 6. Give IUPAC name for the following molecule. Include "cis" and "trans" designations if applicable. H2C-CH3 H -CH2 H- H Br
1. Chair Strain (a) Consider (1R,2S,3S,4S)-1,4-dibromo-2-(tert-butyl)-3-methylcyclohexane. Circle the location (axial or equatorial) for each substituent in this molecule's most stable chair conformer. (b) (၁) Br 1-Br axial equatorial *Bu tBu axial equatorial "CH3 CH 3 axial equatorial Br 4-Br axial equatorial Draw the most stable chair conformer, adding only the substituents (not the hydrogen groups of those stereocenters) onto the chair below. Complete the table below, indicating how many of each type of interaction is present in total for the most stable chair conformer as described in (a). gauche interactions between gauche interactions 1,3-diaxial interactions substituents and the ring between substituents between substituents
Use your answers from Problem 2.48 to complete the table showing correlations between cis,trans and axial,equatorial for disubstituted derivatives of cyclohexane. Draw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3-dimethylcyclohexane, 1,4-dimethylcyclohexane. (a) Indicate by a label whether each methyl group is axial or equatorial.
Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2-C3 bond and draw Newman projections of the most stable and least stable conformations. Use the data in Table 3-5 to assign strain-energy values to each conformation. Which of the eight conformations is most strained? Which is least strained? (a) 2-Methylbutane (b) 2,2-Dimethylbutane (c) 2,3-Dimethylbutane (d) 2,2,3-Trimethylbutane
Following is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?
For the attached question (a), do the positions of the H and CH3 of the back carbon matter? Can they be switched since the front carbon is 'symmetrical' with two hydrogens?
What is the IUPAC name of the following compound? F La -CI O (1R, 3R)-1-cho-3-fluorocyclohexane O (1S, 3S)-1-chloro-3-fluorocyclohexane O (1S, 3R)-1-chloro-3-fluorocyclohexane O (1R, 3S)-1-chloro-3-fluorocyclohexane
Show your all work
2 1 Group activity: Use molecular model to convert the given 3D perspective structure to Newman projection around C-C bond on the template provided. Fill in the substituent for the most stable conformation in the templates provided. H H OH Br OH CH Y/ 3D of most stable conformation ΕΙ Fischer projection of most stable conformation most stable conformation Use the molecular model of chair conformation of cyclohexane and fill in the substituents in the template provided for chair conformation and complete the Newman projections showing only substituents for given molecules. Circle the chair conformation which is more stable. 1) cis-3-isopropylcyclohexanol 2) trans-3-Isopropylcyclohexaol QO
Starting from the Newman projection below, rotate the back carbon to provide the structure in the least stable conformation. (H3C)₂HC H Q IX H^ H H CH3 o
1，1- dimethylcyclobutane and staggered butane，which one has the most angle strain？why？