Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 5.10A, Problem 5.17P
Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.
- a. (S)-propane-1,2-
diol - b. (R)-2-bromobutan 1-ol
- c. (S)-1,2-dibromobutane
- d. (R)-butan-2-ol
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Build a model of (2S,3S)-3-bromo-2-butanol. Rotate the model so its conformation is displayed as a Fischer projection.
Construct a model in which a tetrahedral carbon atom has four different colored model atoms attached to it- red, green, orange and white representing 4 different atoms attached to the central atom.Â
a) Does the atom have a plane of symmetry? why or why not?
b) Now replace the green atom in your model with a second orange atom. Now two of the groups attached to the carbon atom are identical. Does the model now have a plane of symmetry? Describe it.Â
c)A carbon atom has four different groups attached to the stereogenic center. Draw structural formulas for the following compound and mark stereogenic centers with as asterisk: 1-bromobutane, 2-bromobutane, 1,2-dibromobutane, 1,4-dibromobutane, 2,3-dibromobutane.
Glucose is a simple sugar with five substituents bonded to a sixmembered ring.a.Using a chair representation, draw the most stable arrangement of these substituents on the six-membered ring.
b.Convert this representation to one that uses a hexagon with wedges and dashed wedges.
c.Draw a constitutional isomer of glucose.
d.Draw a stereoisomer that has an axial OH group on one carbon.
Chapter 5 Solutions
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global 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
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
Practice Exercise 1
Which of the following factors determines the size of an atom? a. the volume of the nucleus...
Chemistry: The Central Science (14th Edition)
Label each statement about the polynucleotide ATGGCG as true or false. The polynucleotide has six nucleotides. ...
General, Organic, & Biological Chemistry
Real walls are never totally adiabatic. Use your experience to order the following walls in increasing order wi...
Thermodynamics, Statistical Thermodynamics, & Kinetics
Practice Exercise 1
Which of the following factors determines the size of an atom? a. the volume of the nucleus...
Chemistry: The Central Science (13th Edition)
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
- Shown below is Streptomycin, and Neomycin B. Circle and label as many functional groups in these molecules as you can. a. Label each chiral carbon in Streptomycin. How many total stereoisomers exist for Streptomycin? b. Label each chiral carbon in Neomycin B. How many total stereoisomers exist for Neomycin B?arrow_forwardGlucose is a simple sugar with five substituents bonded to a six-membered ring.a. Using a chair representation, draw the most stable arrangement of these substituents on the six-membered ring.b. Convert this representation into one that uses a hexagon with wedges and dashed wedges.c. Draw a constitutional isomer of glucose.d. Draw a stereoisomer that has an axial OH group on one carbon.arrow_forwarda) Draw the enantiomer of this molecule b) Draw a chiral stereoisomer of this molecule c) Draw the enantiomer of the molecule in part B d) Draw an achiral stereoisomer of this moleculearrow_forward
- b) Circle the correct Haworth structure of the four provided below showing the β-isomer of the following Fischer projection. (Look at the attached image) (Please Show your work so I can understand going forward)arrow_forwardConsider the tricyclic structure B. (a) Label each substituent on the rings as axial or equatorial. (b) Draw B using chair conformations for each six-membered ring. (c) Label the atoms on the ring fusions (the carbons that join each set of two rings together) as cis or trans to each other.arrow_forwardUse flat representation of rings, not chair in the drawing. Determine the most and least stable.  Consider the most stable chair for each of these isomers, and then draw the most stable and least stable isomer based on a comparison of the best chair for each one.arrow_forward
- a).Consider the Fischer projections of the following pair of stereoisomers. Name eachstructure in the pair according to IUPAC nomenclature, using appropriate R/S designation to show handedness. b).Draw the missing stereoisomer(s)in this set. Indicate the relationship (enantiomers or diastereomers) between every possible pairing of compounds. Circle a pair of compounds that, if present in equal amounts, will not show optical activity. If one of these compounds has a specific rotation of -7.9owhen isolated, what is the specific rotation of the other?arrow_forwardConsider the following molecules (a-h) and answer the questions below:i. How many chiral carbon does it contains?ii. Does the molecule have any internal plane of symmetry?iii. Identify the molecule whether it is chiral of achiral?iv. Does it rotate the plane of polarized light?v. Is the molecule optically active?vi. Is meso compound present?vii. Draw all possible stereoisomers for the molecule in Fischer projection and label the relationship between each of the isomer.arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Nomenclature: Crash Course Chemistry #44; Author: CrashCourse;https://www.youtube.com/watch?v=U7wavimfNFE;License: Standard YouTube License, CC-BY