Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 5, Problem 45P

(a)

Interpretation Introduction

Interpretation : The structure of ( R )-2-chloropentane needs to be drawn.

Concept Introduction : When four different groups are attached in a single atom then it is called chiral atom. The priority is given to the groups depending on their atomic mass and configuration is decided in such a way that if the increasing order of priority order is clockwise than the configuration is R and if it is anticlockwise then the configuration is S.

(b)

Interpretation Introduction

Interpretation : The structure of ( S )-2-methyl-3-bromohexane needs to be drawn.

Concept Introduction : When four different groups are attached in a single atom then it is called chiral atom. The priority is given to the groups depending on their atomic mass and configuration is decided in such a way that if the increasing order of priority order is clockwise than the configuration is R and if it is anticlockwise then the configuration is S.

(c)

Interpretation Introduction

Interpretation : The structure of (S)-1,3-dichlorobutane should be drawn.

Concept Introduction : When four different groups are attached in a single atom then it is called chiral atom. The priority is given to the groups depending on their atomic mass and configuration is decided in such a way that if the increasing order of priority order is clockwise than the configuration is R and if it is anticlockwise then the configuration is S.

(d)

Interpretation Introduction

Interpretation:The structure of(R)-2-chloro-1,1,1-trifluoro-3-methylbutane should be drawn.

Concept Introduction : When four different groups are attached in a single atom then it is called chiral atom. The priority is given to the groups depending on their atomic mass and configuration is decided in such a way that if the increasing order of priority order is clockwise than the configuration is R and if it is anticlockwise then the configuration is S.

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Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror image for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice. Build molecular models of any of these examples that seem difficult to you. (a) ОН (b) (c) NH, ОН СH—CH—СООН | pentan-2-ol pentan-3-ol alanine (d) 1-bromo-2-methylbutane (e) chlorocyclohexane (f) cis-1,2-dichlorocyclobutane (h) (i) H CH; "H H. H CH, H
a) Considering compounds 2a through 21, identify: ONE PAIR of geometric isomers; TWO PAIRS of enantiomers and THREE PAIRS of identical molecules. b) Give the names, including the configurations, of each of the geometric isomers and of each of the enantiomers. Draw the relevant structures in the space provided in the Answer Booklet. c) Sort compounds 2a, 2b, 2c, 2f and 2k in order of increasing solubility in water and briefly justify your ordering. 2 НО. AH H H anulta HOwno barwolset of ef 28nuor OH 2bc 2c ning) bi 10291 H WH 2 st brbot di OH Lacenoqoid OH to nabio ni one nt at dit st 2e OH "H OH bre 2a 2d 2g 2j H HO 2h 2k HO ...H di al nt o 2f 2i 21
1. (a) A widely prescribed antibiotic (1) is shown below. Copy the structure of this compound into your answer sheet and answer the following questions. HO. H. H2N (1) (i) Circle and label five different functional groups present. (ii) Indicate the geometry (E or Z) of the alkene double bond in the structure. In your answer include the assignment of priorities. (iii) Identify ALL the chiral carbons present in compound (1) by placing an asterisk (*) at the appropriate atoms. (iv) Select ANY ONE of the chiral centres you have identified in part (iii) above and assign the correct Cahn-Ingold-Prelog (R, S) configuration. In your answer include the assignment of priorities.
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