Stereochemistry Quiz #4.

Slides:



Advertisements
Similar presentations
Optical Activity/ Optical Rotation
Advertisements

Optical Activity Enantiomers are different compounds:
Chapter 5: Stereoisomerism
Organic Chemistry 4 th Edition Paula Yurkanis Bruice Irene Lee Case Western Reserve University Cleveland, OH ©2004, Prentice Hall Chapter 5 Stereochemistry.
Organic Chemistry Stereochemistry. Isomers compounds with the same molecular formula but not identical structures.
The study of the three dimensional structure of molecules.
Organic chemistry for medicine and biology students Chem 2311 Chapter 5 Stereochemistry By Prof. Dr. Adel M. Awadallah Islamic University of Gaza.
1 Stereochemistry Prof. Dr. Harno Dwi Pranowo Austrian-Indonesian Center for Computational Chemistry Chemistry Department, FMIPA UGM.
Stereochemistry- Chapter 3
constitutional isomers:
Chapter 5 Stereochemistry
Bio Organic Chemistry Stereochemistry. Review of Isomers.
Chapter 6 Stereochemistry.
Stereoisomerism Nanoplasmonic Research Group Organic Chemistry Chapter 5.
Chapter 5 Stereochemistry.
Chapter 5 Stereochemistry
3 3-1 Organic Chemistry William H. Brown & Christopher S. Foote.
Chapter 15: Chirality Chiral Stereoisomers Enantiomers R or S Enantiomers R or S Diastereomers D or L Diastereomers D or L.
© 2003 Thomson Learning, Inc. All rights reserved General, Organic, and Biochemistry, 7e Bettelheim, Brown, and March.
Chirality Bettelheim, Brown, Campbell and Farrell Chapter 15.
1 Stereochemistry Recall that isomers are different compounds with the same molecular formula. The two major classes of isomers are constitutional isomers.
Chapter 4: Stereochemistry. Introduction To Stereochemistry Consider two of the compounds we produced while finding all the isomers of C 7 H 16 : 2-methylhexame.
Properties of Stereoisomers of Menthols
111 Fall 2008Dr. Halligan CHM 234 Stereochemistry Chapter 5.
1 Organic Chemistry, Third Edition Janice Gorzynski Smith University of Hawai’i Chapter 5 Lecture Outline Prepared by Layne A. Morsch The University of.
Chirality “Handedness”: Right-hand glove does not fit the left hand. An object is chiral if its mirror image is different from the original object. Chapter.
Properties of Chiral Molecules: Optical Activity
Chiral Molecules with Two Stereogenic Centers How many stereoisomers when a particular molecule contains two stereogenic centers?
Fischer Projections Fischer projection: a two- dimensional representation showing the configuration of a stereocenter –horizontal lines represent bonds.
Chapter 5 Stereochemistry Jo Blackburn Richland College, Dallas, TX Dallas County Community College District  2003,  Prentice Hall Organic Chemistry,
CHE 311 Organic Chemistry I Dr. Jerome K. Williams, Ph.D. Saint Leo University.
We have already covered two kinds of isomerism: Constitutional Isomers (structural isomers) Stereoisomers.
Properties of Chiral Molecules: Optical Activity.
Stereochemistry. 2 Chirality Handedness“ Handedness ”: Right glove doesn’t fit the left hand. Mirror-imageMirror-image object is different from the original.
Stereochemistry Chiral Molecules
Constitutional Isomers
Chapter 5 Stereochemistry: Chiral Molecules 1.
Chemistry 2100 Chapter 15. Enantiomers Enantiomers: Enantiomers: Nonsuperposable mirror images. –As an example of a molecule that exists as a pair of.
Chapter 5 Stereochemistry: Chiral Molecules
Chapter 7 - Stereochemistry Enantiomers of bromochlorofluoromethane Non-superimposable mirror images – Enantiomers.
William Brown Thomas Poon Chapter Six Chirality: The Handedness of Molecules.
Chiral Molecules Chapter 5.
Stereochemistry 240 Chem Chapter 5 1. Isomerism Isomers are different compounds that have the same molecular formula.
Isomers Are different compounds with the same molecular formula
Chapter 5 Stereochemistry at Tetrahedral Centers
Stereochemistry & Chiral Molecules
Stereochemistry of organic compounds
Stereochemistry Chiral Molecules
Chapter 5 Stereochemistry at Tetrahedral Centers
Diastereomers Stereoisomers:
Cyclohexane and its Stereochemistry
Stereochemistry Stereochemistry refers to the
9. Stereochemistry.
Chapter 15 Chirality: The Handedness of Molecules
University of California,
Stereoisomerism and Chirality Unit 5.
Only three of a maximum possible four stereoisomers exists for the molecule shown. These include a pair of enantiomers and a single meso compound. Meso.
Stereoisomerism and Chirality Unit 5.
Chapter 5 Stereochemistry: Chiral Molecules
Chapter 9 Stereochemistry.
Isomers In this chapter, we concentrate on enantiomers and diastereomers.
ENANTIOMERIC PAIR mirror images NOT superimposable
Islamic University of Gaza
CH 5-3: A new Stereoisomer - Diastereomers
Chapter 5 Stereochemistry: Chiral Molecules
Chirality - the Handedness of Molecules
Chapter 15 Chirality: The Handedness of Molecules
Chapter 4: Stereochemistry
Presentation transcript:

Stereochemistry Quiz #4

Question The molecules above are (Z) configurations. True (A) False (B) 27

Question Indicate the relationship of the pair of molecules shown.  A. same molecules  B. mirror images  C. different molecules  D. constitutional isomers E. cis and trans isomers

Question Consider the molecule below. What is the maximum number of methyl groups that can be in the equatorial position at the same time? A. 0 B. 1 C. 2 D. 3 E. 4

Question Both cis- and trans-1,2-dimethylcyclohexane are chiral. True (A) False (B)

Question How many of the following compounds contain an internal mirror plane of symmetry? A) 1 B) 2 C) 3 D) 4

Question Which of the following molecules is chiral? B A C D

What is the stereochemical designation of the following molecule? Question What is the stereochemical designation of the following molecule?  A. (R) B. (S) C. non-chiral (achiral)

Question  Indicate the relationship of the pair of molecules shown. A. same molecules B. enantiomers C. diastereomers D. different molecules E. constitutional isomers

Indicate the relationship of the pair of molecules shown. Question Indicate the relationship of the pair of molecules shown. A. same molecules B. enantiomers C. diastereomers D. different molecules E. constitutional isomers

Indicate the relationship of the pair of molecules shown. Question  Indicate the relationship of the pair of molecules shown. A. same molecules B. enantiomers C. diastereomers D. different molecules E. constitutional isomers

Indicate the relationship of the pair of molecules shown. Question  Indicate the relationship of the pair of molecules shown. A. same molecules B. enantiomers C. diastereomers D. different molecules E. constitutional isomers

Indicate the relationship of the pair of molecules shown. Question Indicate the relationship of the pair of molecules shown. A. same molecules B. enantiomers C. diastereomers D. different molecules E. constitutional isomers

Question In the structures above, which is the R-isomer, A or B? H B A Figure Number: 05-03-002UN Title: Thalidomide Caption: Structural formula and ball-and-stick model of thalidomide showing chiral carbon. Notes: The l isomer of thalidomide is a severe teratogen, whereas the d isomer is only a mild teratogen. The S-isomer is an effective sedative. The R- is a teratogen in humans, but not rats. In the structures above, which is the R-isomer, A or B?

What is the stereochemical designation of the following molecule? Question  What is the stereochemical designation of the following molecule? A. (R) B. (S) C. non-chiral (achiral)

Question  What is the stereochemical designation of the indicated chirality center?  A. (R) B. (S) C. non-chiral (achiral)

Indicate the relationship of the pair of molecules shown. Question Indicate the relationship of the pair of molecules shown. A. same molecules B. enantiomers C. diastereomers D. different molecules E. constitutional isomers

Indicate the relationship of the pair of molecules shown. Question Indicate the relationship of the pair of molecules shown. A. same molecules B. enantiomers C. diastereomers D. different molecules E. constitutional isomers

Question: Calculate []D A 1.00-g sample is dissolved in 20.0 mL ethanol. 5.00 mL of this solution is placed in a 20.0-cm polarimeter tube at 25C. The observed rotation is 1.25 counterclockwise. []D = A) -1.25  B) -6.125  C)-12.5  D) +61.25 

Question A sample of a pure R- enantiomer has a specific rotation of – 40°. A mixture of R-/S- enantiomers has an observed optical rotation of + 22°. What is the % ee of the mixture?  A. 55 % ee R  B. 55 % ee S  C. 18 % ee R  D. 0.55 % ee R E. none of the above

Question  If a sample is 50 % ee of R stereoisomer, what is the % R in the mixture? A. 50 B. 100 C. 25 D. 75

Question  If a chemical reaction produces a mixture of 80% R and 20 % S, what is the % ee? 80 60 20 10 4

Question –60° +60° –40° +40° cannot be determined If a sample of the pure R enantiomer of a molecule has a specific rotation of – 40° what is the specific rotation of pure S? –60° +60° –40° +40° cannot be determined

Question +35° –35° It is negative but value cannot be determined.  If the specific rotation of (R)-2-methylhexan-2-ol is –35°, what is the specific rotation of (S)-hexan-2-ol?   +35° –35° It is negative but value cannot be determined. It is positive but value cannot be determined. It cannot be determined.

Question  If a sample of the pure R enantiomer of a molecule has a specific rotation of – 40° and an enantiomeric mixture of that molecule has an 82% ee S, what shoulld be the observed specific rotation of the sample? +40° +8.2° +32.8° –48.7° cannot be determined

Question Calculate the relative proportions of (+)-2-butanol, []D = +13.5o, and (-)-2-butanol, []D = -13.5o, required to give a specific rotation of +0.45o. 50% R : 50% S 90% R : 10% S 3.3 % R : 92.7% S 52% R : 48% S cannot be determined