Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 4, Problem 38P
Interpretation Introduction
Interpretation:
The energy changes from the rotation of C2-C3 bond of 2,3-dimethylbutane and 2,2,3,3-tetramethylbutane are to be determined with all the maxima and minima.
Concept introduction:
Chair conformation: It is the most stable conformation which accurately shows the spatial arrangement of atoms.
Equatorial bonds are parallel to the average plane of the ring while axial bonds are perpendicular to the average plane of the ring.
The conformation having bonds at equatorial position are more stable than those having at axial position.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
(5) For the formula of C5H12O, (a) show your calculation and determine the degrees of unsaturation present, and (b) draw four of the structural/constitutional isomers possible for the formula.
2A2: Apply the concepts of stereocenters, chirality, asymmetry, and the CIP Rules to label enantiomers/ diastereomers and R/S or
E/Z absolute configurations.
These two (2) structures have ambiguous configurations. Provide a wedge and dash structure for the indicated configurational isomer. In
your response, keep the overall structural orientation the same as given. In addition, label all alkenyl FGs as either E or Z in both structures
by showing your work.
&
H3 C CH3
(R, R, R,)
H3CO.
H3CO
CH3
(S, S, S)
CH3
OCH 3
OCH 3
Compound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of
hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the
structure of compound Z.
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• Ignore alkene stereochemistry.
• If more than one structure fits the description, draw them all.
• 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
Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 1PPCh. 4 - Which structure does not represent...Ch. 4 - Prob. 3PPCh. 4 - Draw bond-line formulas for all of the isomers of...Ch. 4 - Prob. 5PPCh. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Practice Problem 4.8 Give names for the following...Ch. 4 - Prob. 9PPCh. 4 - Prob. 10PP
Ch. 4 - Prob. 11PPCh. 4 - Give the structures and IUPAC names for all the...Ch. 4 - Prob. 13PPCh. 4 - Practice Problem 4.14 Show by a calculation (using...Ch. 4 - Practice Problem 4.15 Write structures for the cis...Ch. 4 - Practice Problem 4.16
(a) Write structural...Ch. 4 - Practice Problem 4.17 Write a conformational...Ch. 4 - Practice Problem 4.18
(a) Write the two...Ch. 4 - Prob. 19PPCh. 4 - Practice Problem 4.20 (a) What is the index of...Ch. 4 - Practice Problem 4.21
Zingiberene, a fragrant...Ch. 4 - Practice Problem 4.22 Carbonyl groups also count...Ch. 4 - Prob. 23PCh. 4 - Give systematic IUPAC names for each of the...Ch. 4 - Prob. 25PCh. 4 - Write the structure and give the IUPAC systema.tic...Ch. 4 - 4.27. Write the structure(s) of the simplest...Ch. 4 - Prob. 28PCh. 4 - 4.29. Write structures for the following...Ch. 4 - Prob. 30PCh. 4 - A spiro ring junction is one where two rings that...Ch. 4 - 4.32. Tell what is meant by a homologous series...Ch. 4 - Four different cycloalkenes will all yield...Ch. 4 - 4.34. (a) Three different alkenes yield...Ch. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - 4.37. Write the structures of two chair...Ch. 4 - Prob. 38PCh. 4 - Without referring to tables, decide which member...Ch. 4 - Prob. 40PCh. 4 - 4.41. Which compound would you expect to be the...Ch. 4 - Prob. 42PCh. 4 - 4.43. Write the two chair conformations of each of...Ch. 4 - Provide an explanation for the surprising fact...Ch. 4 - Prob. 45PCh. 4 - 4.46. Specify the missing compounds and/or...Ch. 4 - Consider the cis and trans isomers of...Ch. 4 - Prob. 48PCh. 4 - Open the energy-minimized 3D Molecular Models on...Ch. 4 - 4.50. Open the 3D Molecular Models on the book’s...Ch. 4 - 4.51. Open the 3D Molecular Model on the book’s...Ch. 4 - 1. The predominant conformation for D-glucose is...Ch. 4 - Prob. 2LGPCh. 4 - When 1,2-dimethylcyclohexene is allowed to react...Ch. 4 - Prob. 4LGP
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
- Compounds X and Y both have the formula C7H₁4. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylhexane. The heat of hydrogenation of X is greater than that of Y. Both X and Y react with HCI to give the same single C7H15Cl compound as the major product. What is the structure of X? • In cases where there is more than one answer, just draw one. 23 ▾ Sn [F ChemDoodleⓇ 146arrow_forward(1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case?arrow_forward4.(a). Draw the structures of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4- Dibromocyclohexane. 4(b). Draw the most stable conformers of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4-Dibromocyclohexane. 4(c)Which is more stable? (i) cis-1,4-Dibromocyclohexane or (ii) trans-1,4- Dibromolcyclohexane. Explain the reason for your choice.arrow_forward
- Please tell the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. Also please list how many isomers can be formed in each case.arrow_forwardDifferent position of substituents 1 (a) (b) 58 Construct models, draw the structures and name all the constitutional Isomers of C₂H₂OH. Indicate whether each of these C4 alcohols is 1° (primary), 2° (secondary) or 3° (tertiary). Hint: Identify the type of carbon (1º, 2º, 3º) to which the -OH group is attached. Different functional groups 1. (a) Make models of the isomers of C₂H5O. Write their structures, giving the systematic name of each one, and the family of organic substances to which it belongs.arrow_forwardDraw the correct structure(s) for (2R,3S)-2,3-dibromobutane. Show stereochemistry clearly. explicitly draw all four groups, including wedge/dash bonds, around a chirality center. Indicate whether the compound(s) could exist in an optically active form.arrow_forward
- Cyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq.arrow_forwardStereoisomers share the same connectivity and differ only in the way their atoms are arranged in space. Draw the structure of a compound that is a stereoisomer of cis-1,2-dimethylcyclobutane.(Note that the question asks for a different stereoisomer of the named compound and not the named compound itself.)Use the wedge/hash bond tools to indicate stereochemistry where it exists.In cases where there is more than one answer, just draw one.arrow_forwardCompound W, C6H13Cl, undergoes base-promoted E2 elimination to give a single C6H₁2 alkene, Y. Compound X, C6H13Br, undergoes a similar reaction to form Y and an isomeric alkene Z. W is chiral; X is not. Catalytic hydrogenation of Y and Z produces 2-methylpentane. Propose structures for W and X. 0 • 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. -8) ChemDoodleⓇ Sn [Farrow_forward
- Draw the structure(s) of all of the alkene isomers, C5H10, that contain a branched chain. Consider E/Z stereochemistry of alkenes.arrow_forwardDraw the structure(s) of the cis-cycloalkanes with the chemical formula C6H₁2 that contain a 4-membered ring. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • 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Ⓡ [ ] در <arrow_forwardIn addition to more highly fluorinated products, fluorination of 2-methylbutane yields a mixture of compounds with the formula C5H10F2. Draw the structures of all the isomers with the formula C5H10F2 that would be produced and label with a star all the chiral centers present in their structures.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you