Scribd Logo
Upload

Welcome to Scribd!

  • 195 views

    CHM 1321 Assignment 3 - : Answers

    Uploaded by

    Sara Yuen
    This document contains the answers to an assignment on stereochemistry. It defines constitutional isomers, stereoisomers, and conformers. It provides the chirality or achirality of various compounds with stereocenters and identifies R and S configurations. It includes assigning configurations, drawing 3D structures, converting structures to zig-zag and Fischer projections, and identifying stereochemical relationships between isomers. Distillation or recrystallization can separate diastereomers but not enantiomers.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd

    CHM 1321 Assignment 3 - : Answers

    Uploaded by

    Sara Yuen
    195 views5 pages
    This document contains the answers to an assignment on stereochemistry. It defines constitutional isomers, stereoisomers, and conformers. It provides the chirality or achirality of various compounds with stereocenters and identifies R and S configurations. It includes assigning configurations, drawing 3D structures, converting structures to zig-zag and Fischer projections, and identifying stereochemical relationships between isomers. Distillation or recrystallization can separate diastereomers but not enantiomers.

    Original Title

    Assignment 3

    Copyright

    © Attribution Non-Commercial (BY-NC)

    Available Formats

    PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    This document contains the answers to an assignment on stereochemistry. It defines constitutional isomers, stereoisomers, and conformers. It provides the chirality or achirality of various compounds with stereocenters and identifies R and S configurations. It includes assigning configurations, drawing 3D structures, converting structures to zig-zag and Fischer projections, and identifying stereochemical relationships between isomers. Distillation or recrystallization can separate diastereomers but not enantiomers.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    195 views5 pages

    CHM 1321 Assignment 3 - : Answers

    Uploaded by

    Sara Yuen
    This document contains the answers to an assignment on stereochemistry. It defines constitutional isomers, stereoisomers, and conformers. It provides the chirality or achirality of various compounds with stereocenters and identifies R and S configurations. It includes assigning configurations, drawing 3D structures, converting structures to zig-zag and Fischer projections, and identifying stereochemical relationships between isomers. Distillation or recrystallization can separate diastereomers but not enantiomers.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 5

    CHM 1321 Assignment 3 - ANSWERS

    1) Identify each of the following pairs as constitutional isomers, stereoisomers (configurational isomers), or conformers.
    a) + Stereoisomers b) + Constitutional isomers c) + Same compound f) Br Br + Br e) Br Br + Br d) Br Br + Br Stereoisomers Br

    Br

    Constitutional isomers Br

    conformers (conf ormational isomers)

    2) Draw each structure below along with its mirror image. Indicate whether the compound is chiral or achiral. a) cis-1,2-dimethylcyclopentane. b) trans-1,2-dimethylcyclopentane
    a) CH3 CH3 H3C H3C b) CH3 CH3 H3C H3C

    Achiral - mirror images are superimposable plane of symmetry exists (meso compound)

    Chiral - mirror images are not superimposable

    c) cis-1,3-dimethylcyclohexane d) trans-1,3-dimethylcyclohexane
    CH3 c) H3C d) CH3 H3C

    CH3 CH3 CH3 CH3 Achiral - mirror images are superimposable Chiral - mirror images are not superimposable plane of symmetry exists (meso compound) O O O O

    e)

    f)

    Achiral - mirror images are superimposable - no stereogenic centre, 2 identical groups on tetrasubstituted carbon Plane of symmetry exists

    Chiral - mirror images are not superimposable

    Assignment 3 - Answers Question 2 contd: g) CH3CClBrH h) (CH3)2CHOH


    g) Br Cl Cl Br

    i) CH3CH2CHOHCH3
    h) OH

    j)CH3CH2CHOHCH2CH3
    HO

    Chiral - mirror images not superimposable i) OH OH j)

    Achiral - mirror images superimposable (2 identical groups on central carbon)

    OH

    OH

    Chiral - mirror images not superimposable

    Achiral - mirror images superimposable (2 identical groups on central carbon) Plane of symmetry exists

    3) Identify the chiral centres in the following molecules: (indicated with a *) a. fexofenadine (Allegra):
    CO2 H N OH

    *
    OH

    b.

    Indinavir (Crixivan):
    N N O N OH OH

    *
    N H

    *
    C(CH3 )3

    *
    O

    H N

    Assignment 3 - Answers 4) Draw each of the following compounds in three dimensions. Draw the mirror image of each and determine whether the compounds are chiral. For all chiral compounds, determine whether the configuration of each stereogenic centre is R or S. a) 1,3-dibromobutane b) 2-butanol c) 2-methylpentane d) 3-methylpentane e) 3-methylhexane f) 1,2-dihydroxypropane g) 1, 2, 4-trihydroxybutane
    (Priorities in red) Br
    2 4H 1 R 3 3 S 2 2 3 3 4H 2

    a)

    Br

    b)

    c)
    1

    Br

    Br Chiral

    4H

    4H OH 1

    OH Achiral
    4H 1 1

    Chiral

    4H

    3 S

    4H 3 2 R

    OH
    R

    H OH OH HO
    S 2 3

    d) Achiral
    4 1OH

    e)
    1

    f)
    1 3

    Chiral

    Chiral

    H OH
    S 3

    g) HO

    OH HO
    2

    Chiral

    OH

    5) For the following compounds, show the stereogenic center(s) by labeling them with a star (*) and determine the configuration of each centre (R or S).
    Priorities in red
    4 1 1

    H *
    R

    Cl HO
    2

    CH3

    b)

    2 S 1

    Br R H * CH2CH3 H3C
    4 3 2 2

    S 2

    c)

    Cl

    *
    4H 1OH

    Br

    d)

    2 4H 3

    S 1

    *
    4

    H H H
    2 3

    Br * H4
    3 1

    CHO S f) 3 * CHCH 2 (CH3O)2HC CH(CH3)2 1


    4

    O g)
    3 4H 1 R 2

    h)

    CO2H * (back) H R

    *S
    3 R

    O * OR
    2 3

    i)

    j) H C S 3 1 3 * H4

    O O

    k)
    S

    * * *

    l)
    R

    OH

    * CH3
    4

    NH2

    3 4H R 2 R

    *
    3 S

    * * OH H4
    1 2

    * *

    *
    2

    * OH H 1
    4

    OH

    Assignment 3 - Answers 6) Phenylalanine has the following structure, given that the configuration is S, what is the proper way to draw the compound?
    One way to approach this problem is to draw the chiral center in your favourite conformation (arbitrary) and assign R or S to it. If you've drawn the S conformer, you've answered the question. If not, switch any two groups to obtain the opposite conformer.

    H2N O

    OH

    S H2N O

    OH

    7) Assign the configuration at each stereogenic centre. Convert the following to Fischer projections.
    Br a) H HO
    2

    CH 3 Br
    1 S

    b)

    H H3 C
    2 3 1

    c)

    Cl Cl
    3 4

    OH

    d)

    HO
    4H

    CH 3
    3

    H 3C
    4H

    Ph
    S

    CH2 OH H Cl 1 S CH2 Cl
    2

    H3 C
    3 2

    1 S

    Ph =

    OH H e) O O CHCH 2 CH(CH 3 )2 O 1 O
    4H S 3 2

    OH CHO g) H 2N O
    2 3 R

    f ) HO OH

    h) OH HO

    OH OH OH
    2

    OH

    O CO2 H OH 3 H
    4 2

    CHO HO H S HO HO HO HS HS H S OH

    CO 2H H4 NH 2
    1

    CO 2H H OH 1 H CO 2H
    3

    HO

    H R HO
    1

    CO2 H

    Br i) H H CH 3 CH 2CH3 Cl OH priorities
    3 3

    CH3 H H H H Br S Br R

    CH 2CH3 Cl HR HO HS CH 3

    j)

    Br H3 C

    priorities
    1

    CH 2CH3 Cl HR 4 2 HO H CH 3
    1

    Cl HO
    1

    CH 2CH3 H HS
    4

    CH 3

    H S Br H 2 Br

    CH 3 H Br
    2 4H 3 R

    Br 1

    CH 3

    Assignment 3 - Answers 8) Convert the following to zig-zag structures (line structures). Assign the configuration at each stereogenic centre.
    a) COOH HO H CH3 OH OH S O S O b) COOH H CH3 NH2 NH2 OH c) CH2CH2OH H Br CH3 Br R OH R H d) H CH2OH Cl Br CH3 Br S Cl OH

    e)

    CH2OH H OH H OH CH3 OH R S OH OH

    f)

    H Br

    CH2OH OH OH CH3

    g)

    HO Br S S OH OH

    H HO H H

    CHO OH H OH OH OH

    H3CS H CH3CONH O

    h)

    H SCH3 OH H CH3 NH S R OH S S

    HO

    OH OH R CHO S R R OH OH

    9) Give the stereochemical relationship between each pair of isomers (enantiomers, diastereomers, meso compounds). USE A MODEL!
    a) CH3 H OH H OH CH3 CH3 HO H HO H CH3 CH2 OH CH 2OH H OH HO H b) H HO H OH CH 3 CH3 Enantiomers c) CH 3 Br H Cl Br Cl H CH3

    Meso Compound

    Same Compound

    OH d) OH Enantiomers Cl f) g) H diastereomers C HO OH e) HO N

    OH N

    Same Compound Br C H H Cl h) Br Br Br enantiomers

    CH 3 H

    H 3C

    enantiomers

    10) Which of the following pairs of compounds could be separated by a method such as distillation or recrystallization? a. Diastereomers separable b. Enantiomers not separable c. Diastereomers separable 5

    You might also like