Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 5, Problem 5.38SP
3,4-Dimethylpent-1-ene has the formula CH2=CH—CH(CH3)—CH(CH3)2. When pure (R)-3,4-dimethylpent-1-ene is treated with hydrogen over a platinum catalyst, the product is (S)-2,3-dimethylpentane.
- a. (a) Draw the equation for this reaction. Show the stereochemistry of the reactant and the product.
- b. (b) Has the chiral center retained its configuration during this hydrogenation, or has it been inverted?
- c. (c) The reactant is named (R), but the product is named (S). Does this name change imply a change in the spatial arrangement of the groups around the chiral center? So why does the name switch from (R) to (S)?
- d. (d) How useful is the (R) or (S) designation for predicting the sign of an optical rotation? Can you predict the sign of the rotation of the reactant? Of the product? (Hint from Juliet Capulet: “What’s in a name? That which we call a rose/By any other name would smell as sweet”)
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
draw out the following structures plese
Draw everything on a piece of paper outlining the synthesis from acetaldehyde to 2 cyclopentene carboxaldehyde using carbon based reagants with 3 carbons or fewers. Here is the attached image.
Manoharan Mariappan, FR.D.,
34) Complete the following reaction starting from hex-1-yne proceeding via different substitution reactions forming
2-heptanone.
(25 pts).
A
Sia₂BH
H₂O₂
NaOH
Br
D
Mechanism for reaction D - ether-cleavage:
10
B
Ph-MgCI, THF
H₁₂O+
D
HBr (XS)
C
TsCl, Py
CH3-CH2-CH2-ONa
Chapter 5 Solutions
Organic Chemistry (9th Edition)
Ch. 5.2 - Determine whether the following objects are chiral...Ch. 5.2A - Prob. 5.2PCh. 5.2B - Prob. 5.3PCh. 5.2B - Prob. 5.4PCh. 5.2C - Prob. 5.5PCh. 5.3 - Prob. 5.6PCh. 5.3 - Prob. 5.7PCh. 5.4D - Prob. 5.8PCh. 5.4D - Prob. 5.9PCh. 5.4D - Prob. 5.10P
Ch. 5.5 - Prob. 5.11PCh. 5.7 - When optically pure (R)-2-bromobutane is heated...Ch. 5.7 - Prob. 5.13PCh. 5.8 - Prob. 5.14PCh. 5.9B - Draw three-dimensional representations of the...Ch. 5.10A - For each sot of examples, make a model of the...Ch. 5.10A - Draw a Fischer projection for each compound....Ch. 5.10B - Prob. 5.18PCh. 5.10C - For each Fischer projection, label each asymmetric...Ch. 5.11C - Prob. 5.20PCh. 5.13 - Prob. 5.21PCh. 5.13 - Prob. 5.22PCh. 5.15 - Prob. 5.23PCh. 5.16A - Prob. 5.24PCh. 5 - The following four structures are naturally...Ch. 5 - For each structure, 1. star () any asymmetric...Ch. 5 - Prob. 5.27SPCh. 5 - Prob. 5.28SPCh. 5 - Prob. 5.29SPCh. 5 - Prob. 5.30SPCh. 5 - Prob. 5.31SPCh. 5 - Prob. 5.32SPCh. 5 - Prob. 5.33SPCh. 5 - Prob. 5.34SPCh. 5 - For each structure, 1. draw all the stereoisomers....Ch. 5 - Prob. 5.36SPCh. 5 - Prob. 5.37SPCh. 5 - 3,4-Dimethylpent-1-ene has the formula...Ch. 5 - A graduate student was studying enzymatic...Ch. 5 - Prob. 5.40SPCh. 5 - Prob. 5.41SP
Additional Science Textbook Solutions
Find more solutions based on key concepts
1. Rub your hands together vigorously. What happens? Discuss the energy transfers and transformations that take...
College Physics: A Strategic Approach (3rd Edition)
Gregor Mendel never saw a gene, yet he concluded that some inherited factors were responsible for the patterns ...
Campbell Essential Biology (7th Edition)
Why do scientists think that all forms of life on earth have a common origin?
Genetics: From Genes to Genomes
Sea turtles have disappeared from many regions, and one way of trying to save them is to reintroduce them to ar...
MARINE BIOLOGY
Describe the evolution of mammals, tracing their synapsid lineage from early amniote ancestors to true mammals....
Loose Leaf For Integrated Principles Of Zoology
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
- In the table below, the correct structure for (2R)-3-methylpentan-2-ol (IUPAC name) can be represented by the letter OH OH HE > ' ÕH C B OH D A/ E OHarrow_forwardPredict the major products of the following organic reaction: + A Δ ? Some important notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. Check Click and drag to start drawing a structure. Save For Later 2025 McGraw Hill LLC. All Rights Reserved. Terms of Usearrow_forwardWhy is analysing salt content (using Mohr titration) in both regular & salt reduced tomato sauce important?arrow_forward
- In the image below, correctly name the glassware # _P ( Blank 1) and T ( Blank 2). 景 A W Blank # 1 Blank #2 1000 +19 E E D 0 0-0 G H A A K Π 12 R M N S 0-0-arrow_forwardFeedback: Your answer is incorrect. Predict the major products of the following organic reaction: CN Δ + A ? NC Some important notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. esc Check 80 MH F1 F2 F3 F4 F5 50 @ # C % 95 € Save For Later Sub 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy C A DII F6 F7 F8 7 * 8 Λ & 6 F9 F10 9 0 4arrow_forwardIncorrect Feedback: Your answer is incorrect. Predict the major products of the following organic reaction: ཤིགས་བྱ རྩ་ཅད་ཀྱིས་༢༩ + Some important notes: A ^ ? • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. E Check 0 لا Save For La ©2025 McGraw Hill LLC. All Rights Reserved. Terms of All F9 Aarrow_forward
- Predict the major products of the following organic reaction: + Δ A ? Some important notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. Explanation Check Click and drag to start drawing a structure. 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privaarrow_forwardesc 2 Incorrect Feedback: Your answer is incorrect. Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? ? A O • If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. . If your answer is no, check the box under the drawing area instead. Check F1 ! @ X C Save For Later Submit Assignment 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility 80 et A ད 1 4 F2 F3 F4 F5 F6 F7 F8 F9 F10 F11 F12 # $ 45 % A 6 87 & * 8 9 ) 0 + ||arrow_forwardCan the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating the reactants? ?A Δ O • If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like. • If your answer is no, check the box under the drawing area instead. Explanation Check Click and drag to start drawing a structure. 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibilit ku F11arrow_forward
- १ eq ine teaching and × + rn/takeAssignment/takeCovalentActivity.do?locator-assignment-take [Review Topics] [References] Write an acceptable IUPAC name for the compound below. (Only systematic names, not common names are accepted by this question.) Keep the information page open for feedback reference. The IUPAC name is In progress mit Answer Retry Entire Group 5 more group attempts remaining Cengage Learning | Cengage Technical Support Save and Exitarrow_forwardDraw the molecules.arrow_forwardDraw the mechanism for the acid-catalyzed dehydration of 2-methyl-hexan-2-ol with arrows please.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
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