Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 4.14, Problem 49P
Which of the following compounds has a stereoisomer that is a meso compound?
- A. 2,4-dibromohexane
- B. 2,4-dibromopentane
- C. 2,4-dimethylpentane
- D. 1,3-dichlorocyclohexane
- E. 1,4-dichlorocyclohexane
- F. 1,2-dichlorocyclobutane
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Organic Chemistry
Explain your solution in a step by step fashion. Explain everything clearly and do not leave out any major or minor steps or details. Provide a thoughtful explanation to the question. In other words, provide your reasoning for why you picked your answer. Why are the molecules enantiomers? etc
(a) how many stereoisomers are possible?
(b) how many chiral carbons are in the structure?
(c) is this optically active?
Which of the following compounds has a stereoisomer that is a meso compound? A 2,4-dibromohexane
B 2,4-dibromopentane
C 2,4-dimethylpentane
D 1,3-dichlorocyclohexane
E 1,4-dichlorocyclohexane
F 1,2-dichlorocyclobutane
Chapter 4 Solutions
Organic Chemistry (8th Edition)
Ch. 4.1 - Prob. 2PCh. 4.1 - Prob. 3PCh. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.1 - Which of the roll owing compounds have a dipole...Ch. 4.2 - Draw and label the E and Z isomers for each of the...Ch. 4.2 - Assign relative priorities to each set of...Ch. 4.2 - Tamoxifen slows the growth of some breast tumors...Ch. 4.2 - Prob. 10PCh. 4.2 - Name each of the following:
Ch. 4.2 - Draw the Z isomer of an alkene that has a CH3 and...Ch. 4.3 - Prob. 13PCh. 4.4 - Prob. 14PCh. 4.5 - Prob. 16PCh. 4.6 - Prob. 17PCh. 4.7 - Prob. 18PCh. 4.8 - Prob. 20PCh. 4.8 - Prob. 22PCh. 4.8 - Prob. 23PCh. 4.8 - Prob. 24PCh. 4.8 - Draw a perspective formula for each or the...Ch. 4.8 - Prob. 27PCh. 4.9 - Prob. 28PCh. 4.9 - What is the configuration of the following...Ch. 4.9 - Prob. 32PCh. 4.10 - Prob. 33PCh. 4.10 - (S)-(+)-Monosodium glutamate (MSG) is a flavor...Ch. 4.11 - Prob. 35PCh. 4.11 - Prob. 36PCh. 4.12 - Prob. 38PCh. 4.12 - Prob. 39PCh. 4.12 - The stereoisomer of cholesterol found in nature is...Ch. 4.12 - Prob. 41PCh. 4.13 - 1-Bromo-2-methylcyclopentane has four pairs of...Ch. 4.13 - Prob. 43PCh. 4.13 - Draw all possible stereoisomers for each of the...Ch. 4.13 - Prob. 45PCh. 4.13 - Of all the possible cyclooctanes that have one...Ch. 4.13 - Prob. 47PCh. 4.13 - Prob. 48PCh. 4.14 - Which of the following compounds has a...Ch. 4.14 - Draw all the stereoisomers for each of the...Ch. 4.15 - Prob. 52PCh. 4.15 - Name the isomers you drew in Problem 52.Ch. 4.15 - Chloramphenicol is a broad-spectrum antibiotic...Ch. 4.15 - Draw a perspective formula for each of the...Ch. 4.15 - Name the following:Ch. 4.15 - Prob. 57PCh. 4.15 - Prob. 59PCh. 4.15 - Convert the perspective formula to a skeletal...Ch. 4.15 - Prob. 62PCh. 4.16 - Prob. 63PCh. 4.17 - Limonene exists as two different stereoisomers....Ch. 4 - a. Draw three constitutional isomers with...Ch. 4 - Prob. 65PCh. 4 - Prob. 66PCh. 4 - Which of the following has an asymmetric center?...Ch. 4 - Prob. 68PCh. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Prob. 71PCh. 4 - Assign relative priorities to each set of...Ch. 4 - Prob. 73PCh. 4 - Which of the following are optically active?Ch. 4 - Prob. 75PCh. 4 - Name the following:Ch. 4 - Which of the following has an achiral...Ch. 4 - Using skeletal structures, draw the stereoisomers...Ch. 4 - Prob. 79PCh. 4 - Citrate synthase, one of the enzymes in the series...Ch. 4 - Prob. 81PCh. 4 - Prob. 82PCh. 4 - Prob. 83PCh. 4 - Prob. 84PCh. 4 - Prob. 85PCh. 4 - Prob. 86PCh. 4 - Prob. 87PCh. 4 - Prob. 88PCh. 4 - Prob. 89PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 91PCh. 4 - Prob. 92PCh. 4 - Draw structures for the following: a....Ch. 4 - For each of the following structures, draw the...Ch. 4 - Prob. 95PCh. 4 - Prob. 96PCh. 4 - Prob. 97PCh. 4 - a. Using the wedge-and-dash notation, draw the...Ch. 4 - Prob. 99PCh. 4 - Prob. 100PCh. 4 - Prob. 101PCh. 4 - a. Draw the two chair conformers for each of the...Ch. 4 - Prob. 103PCh. 4 - Is the following compound optically active?Ch. 4 - Prob. 105P
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
- An experiment (a set of experiments) that would allow you to decide whether this reaction is stereospecific. stilbene ---Br2, Acetic acid--> stilbene dibromide .arrow_forwardWhich of the following compounds show geometrical isomerism? a. 1-Clorobut-1-ene b. 1,2-Dichlorobut-1-ene c. 1,1-Dichlorobut-1-ene d. 1-Clorobut-2-ene e. 1,3-Dimethylcyclohexane b,d,e c a,c,d a,e a,b,d,earrow_forwardQ)Explain with an example. a) Markovnikov’s rule. b) Zaitsev’s rule.arrow_forward
- Organic Chemistry HW: CANNOT BE HAND DRAWN 2,6-dimethyloct-2-ene Provide a detailed typed explanation of Stereoisomers show the expanded structure of your molecule. Calculate the maximum number of possible stereoisomers of your molecule using the following formula: Maximum number of possible stereoisomers = 2n (where n= the number of chiral carbons in your molecule). This calculation does not include E- or Z- isomers for any compounds containing double bonds Type or using a computer program "draw" the possible stereoisomers of the molecule. Note that E-, Z- isomers of each stereoisomer are also possible and would not be accounted for by the formula above; draw any E- or Z- isomers.arrow_forward"Trans alkenes are more stable than cis alkenes because they have fewer steric interactions" What this statement says ?arrow_forwardDraw the structure of each molecule below and put an asterisk on each tetrahedral stereocenter. i) 3,4-dichlorohexane ii) 3-bromo-1-iodo-5-methylhexane iii) 3-bromo-2,4-dimethylpentanearrow_forward
- Why are these two structures enantiomers? They look more like structural isomers to me.arrow_forward1.Circle the organic the functional groups and name them. 2.Mark all chiral centers and determine the configuration of one of them.arrow_forwardFor which double bonds are stereoisomers possible?arrow_forward
- determine the chiral centers in the "Morphine". and draw the stereoisomer of the morphine.arrow_forwardIn 1935, J. Bredt, a German chemist, proposed that a bicycloalkene could not have a double bond at a bridgehead carbon unless one of the rings contains at least eight carbons. This is known as Bredt’s rule. Explain why there cannot be a double bond at this 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
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry: Matter and ChangeChemistryISBN:9780078746376Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl WistromPublisher:Glencoe/McGraw-Hill School Pub Co
Chemistry: Matter and Change
Chemistry
ISBN:9780078746376
Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
Publisher:Glencoe/McGraw-Hill School Pub Co
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