the plan IS. CH3 -Br CH3 mirror plane Shown below is a representation of 2-bromobutane. a. Draw the mirror image of this representation. b. Build a model of each structure. Are the two structures superimposable? 2. c. Indicate the configuration of each structure shown below using the Cahn- Ingold-Prelog R/S notation system. CH3" -Br CH;CH2 mirror plane 3. Draw the Fisher projection of the R enantiomer of 2-bromobutane below. I'

the plan IS. CH3 -Br CH3 mirror plane Shown below is a representation of 2-bromobutane. a. Draw the mirror image of this representation. b. Build a model of each structure. Are the two structures superimposable? 2. c. Indicate the configuration of each structure shown below using the Cahn- Ingold-Prelog R/S notation system. CH3" -Br CH;CH2 mirror plane 3. Draw the Fisher projection of the R enantiomer of 2-bromobutane below. I'

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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3. Determine the relationship for the following pairs of structures. Use "E" for enantiomers, "D" for diastereomers, "C" for constitutional isomers, "S" for same, and "NS" (not same) for different compounds. a. b. с. d. е. f. Н н iPr "Де Br Br OH CH3 CH3 Ή OH OH OH Br Br CH3 CH3 Br -Н НО -Н H3C -ОН COOH Br Br Br Н H3C- Br OH CH3 Н CH3 iPr CH3 Н- -Br НО _H H OH OH CH3 ОН -OH COOH
1. Consider the structure shown on the right and answer the following questions about it (fill in blanks or circle proper choice). H 14. 1+0 140 H a. Its molecular formula is CHO and so it fits the general formula for a carbohydrate, which is C,( ). b. Specifically, this structure is (a D/ an L) (aldo/keto) (pent/hex) (ase/ose). c. Will it be optically active? d. If the top carbon was converted to a CH₂OH, would it be optically active? e. This molecule can form a six membered ring by addition of one of its -OH groups to the C-O group. Draw a circle around the -OH group which would lead to this ring. This is called a (furanose/pyranose) ring. Draw the structure of this ring in the space on the right. f. This molecule can also form a five membered ring by addition of one of its -OH groups to the C-O group. Draw a square around the -OH group which would lead to this ring. This is called a (furanose/pyranose) ring. g. In each of the rings referred to in parts e and f the carbonyl carbon…
5. CH3COOH CH3CH2OCOCH3 + H20 -COCH3 6. (6a)_ (6b)_- + H2O -СООН (7а) + 2 NaOH _(7b + NazCOs. +. H2O 7.
4. Designate the correct descriptors (R or S for each stereocenter and E or Z for each double bond) for each of the molecules listed. Include your rationale for assigning priority using the Cahn-Ingold-Prelog priority rules. a. 5 [10 markal OH b. asa EN C. مطمئو 2H
Draw the structure of the final product(s) of this series of reactions. 1. Brz 2. 3 equivalents of NANH2 3. mild acid 4. BH3 5. H,O2/ NaOH • Use the wedge hash bond tools to indicate stereochemistry where it exists. Include H atoms at chiral centers only. • If a group is achiral, do not use wedged or hashed bonds on it. • Draw organic species only. • Do not include lone pairs in your answer. They will not be considered in the grading. If the reaction produces a racemic mixture, draw both stereoisomers. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the - sign from the drop-down menu.
HOCH2CH2OH O: H* Br2 (excess) 7. NaOCH3 C6H5 CH3OH 5. 6.
geraniol OH Reagents a. SOCI₂ b. CH3COCI C. CH₂(CO₂Et)2, CH3CH₂O* Na* d. H3O*, heat e. CH3COCH₂CO₂Et, CH3CH₂O Na* f. CH3CH₂OH geranylacetone Select reagents from the table to carry out this conversion. Enter your answer as a string of letters without spaces or punctuation, i.e. ace.
3. Assign and label R/S configuration for all stereogenic centers and assign E/Z to all alkenes on the molecules below. Note: Read and work through Interchapter C for further description of CIP rules and to further understand how to assign R/S configuration and E/Z configurations. CI H3C, ОН (H3C)3C Br b. O2N ОН d. а. с. Br
2. In aqueous solution d-glucose (or dextrose) exists in equilibrium between a linear and cyclic form shown below. A. Mark all the stereocenters in the linear form of the molecule. Number them 1,2,3, etc. B. Draw out the reaction that converts the linear form to the 6-membered ring using the arrow formalism. C. Identify the stereocenters in the 6-member ring that correspond to the stereocenters in the linear form marking them as 1,2,3, etc. The reaction also created a new stereocenter. Mark it as H -OH HO--H H--OH нон Ho но HO HO H он H-OH H но.
5. Circle all of the following that are optically active. Convert these structures to whatever format you prefer to determine if they are optically active or not. Put a box around any meso compounds. H. CI H H CH3 CH3 H- HO- CI H b. CI CI с. Нас Br d. NH2 а. Ме HO CH3 H. H3C HO H H. ČH3 f. Ме h. H Br е. g. -use models to visualize (h) and its mirror image -consider hybridization of central C -redraw (h) showing p-orbitals of -bonds above
3. Indicate whether each of the following structures is (R)-2-chlorobutane or (S)-2-chlorobutane (if necessary, use models). a. CH₂CH₂ CH3 H CH3 b. H+C CH₂CH3 d. e. f. H₂C- H H H H CH3 CH3 H CH3 H CI
Which compounds contain stereocentres? I. 2-methylpentane II. chlorocyclohexane III. 3-methyl-2-butanol IV. 2-hydroxypropanoic acid Select one: O a. I, II O b. III, IV O c. I, III O d. II, IV