Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Textbook Question
Chapter 7, Problem 2E
Label each of the following as cis, trans or neither. Below each structure that is cis draw a transconfigurational stereoisomer or vice versa.
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(a) Using Newman projections, draw all staggered and eclipsed conformations that result from rotation around the indicated
bond in each molecule; (b) draw a graph of energy versus dihedral angle for rotation around this bond.
[1] CH3CH₂ CH₂CH₂CH3 [2] CH3CH₂ CHCH₂CH3
TCH₂
Answer the following questions and upload your answer.
A. Draw the two chair conformations of cis-1-isopropyl-3-methylcyclohexane. Write under your drawing which conformation is the most stable one.
B. Would the trans isomer be more stable than the cis isomer? Why?
Label following pairs of molecules as being either same same structure, completely different, constitutional isomers, or stereoisomers.
Chapter 7 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 7 - Prob. 1CTQCh. 7 - Prob. 2CTQCh. 7 - Prob. 3CTQCh. 7 - Draw wedge and dash skeletal representations of...Ch. 7 - Label each ring in Figure 7.2 cis or trans.Ch. 7 - Prob. 6CTQCh. 7 - Prob. 7CTQCh. 7 - Prob. 8CTQCh. 7 - a model of cyclohexane in a chair conformation,...Ch. 7 - Prob. 10CTQ
Ch. 7 - Prob. 11CTQCh. 7 - Fill in the blanks: cis-1,3-Dimethylcyclohexane...Ch. 7 - Prob. 13CTQCh. 7 - Prob. 14CTQCh. 7 - Prob. 15CTQCh. 7 - Prob. 16CTQCh. 7 - Prob. 17CTQCh. 7 - Prob. 18CTQCh. 7 - Draw chair representations of...Ch. 7 - Which stereoisomer in the previous question is...Ch. 7 - Prob. 21CTQCh. 7 - Prob. 1ECh. 7 - Label each of the following as cis, trans or...Ch. 7 - Which pair has more in common with one another?Ch. 7 - Prob. 4ECh. 7 - Prob. 5ECh. 7 - Prob. 6ECh. 7 - Fill in the table by drawing a representation of a...Ch. 7 - Prob. 9ECh. 7 - True or False: If you perform a chair flip on...Ch. 7 - Prob. 11ECh. 7 - Prob. 12ECh. 7 - Prob. 13ECh. 7 - Prob. 14ECh. 7 - Prob. 15ECh. 7 - Draw trans-1-tert-butyl-3-methylcyclohexane in its...Ch. 7 - Build a model of methylcyclohexane, and use the...
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- Draw Newman Projections of the following molecule, looking down the C2-C3 bond. Under A, draw the anti conformation, under B, draw a Gauche conformation, under C, draw the least stable eclipsed conformation. A B Carrow_forwardLabel the following pairs as A) distereoisomers, B) enantiomers, C) conformers, or D) the same. b1 c1 d1 e1 a2 b2 c2 The structures above are labeled a1, a2, b1, b2 ...etc. Using these labels, indicate which compounds above would have an optical rotation ofarrow_forwardReview Topics) [References) Indicate whether the pair of structures shown represent stereoisomers, constitutional isomers, different conformations of the same compound, or the same conformation of a compound viewed from a different perspective. Note that cis, trans isomers are an example of stereoisomers. H2N- H2N. -NH2 NH2 CI CH3. CH3- CH3 H ČH3 H. Submit Answer Retry Entire Group 9 more group attempts remainingarrow_forward
- The energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).arrow_forward1: Draw the chain conformer of... 1a. Cyclohexane, label all the axial and equatorial hydrogens 1b. The most stable conformer of ethylcyclohexane 1c. The most sable conformer of trans-1-tert-butyl-3-methylcyclohexanearrow_forward3) Draw a cyclohexane chair with 3 substituents in the most stable conformation. Explain why the conformation you've chosen is the most stable.arrow_forward
- Draw the three constitutional isomers having molecular formula C7H14 that contain a five-membered ring and two methyl groups as substituents. For each constitutional isomer that can have cis and trans isomers, draw the two stereoisomers.arrow_forward- Consider 1-bromopropane(propyl bromide). I) Draw a Newman projection (conformation) in which methyl and bromine are anti. II) Draw a Newman projection (conformation) in which methyl and bromine are in gauche. II) Draw a Newman projection (conformation) which represents the least stable eclipsed conformation.arrow_forwardPyrethrin II and pyrethrosin are two natural products isolated from plants of the chrysanthemum family. Pyrethrin II is a natural insecticide and is marketed as such. Q,) Label all chiral centers in each molecule and all carbon-carbon double bonds about which there is the possibility for cis,trans isomerism.arrow_forward
- In this question, you will draw all the constitutional isomers of CH4Br₂. This compound has an IHD of 1, which means it will either have one ring or one double bond. For this question, do not consider stereoisomers.arrow_forwardAnswer the following questions about compound A, which contains a CH3 group and OH group bonded to the carbon skeleton that consists of three six-membered rings in the conformation shown a.) Are the CH3 and OH groups oriented cis or trans to each other?b.) Is a substituent on Ca that is cis to the CH3 group located in the axial or equatorial position? c.) Is an equatorial Br at Cb oriented cis or trans to the OH group?d.) Is the H atom on Cc located cis or trans to the OH group?e.) Is a substituent on Cd that is trans to the OH group located in the axial or equatorial position?arrow_forwardBased on the structures of lycopene and β-carotene, which are two chemicals found in another common vegetable, the tomato, answer the following questions: 1. Are they stereoisomers, constitutional isomers or not even isomers? 2. Do you expect them to be relatively polar or nonpolar substances? Why? 3. How many double bonds are in lycopene? How many in β -carotene? 4. As lycopene is transformed into β -carotene, how many pi electrons from the double bonds are transformed into single bonds? How many new single bonds are being formed in β -carotene? 5. The first step of a possible mechanism for the ring closure in the transformation is outlined below (only part of the structure is shown for simplicity). Draw the product that results from this arrow pushing mechanism. Be sure to include any formal charges that arise from the carbon atoms.arrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License