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Draw the structures of the following compounds. (Includes

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 33SP Chapter 10

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 33SP

Problem 33SP

Draw the structures of the following compounds. (Includes both new and old names.)

(a) triphenylmethanol

(b) 4-(chloromethyl)heptan-3-ol

(c) 2-cyclohexen-1-ol

(d) 3-cyclopentylhexan-3-ol

(e) meso-2,4-pentanediol

(f) cyclopentene glycol

(g) 3-(iodomethyl)phenol

(h) (2R,3R)-2,3-hexanediol

(i) cyclopent-3-ene-1-thiol

(j) dimethyl disulfide

(k) 3-methylhex-4-yn-2-ol

Step-by-Step Solution:
Step 1 of 3

Solution 33SP

(a) Triphenylmethanol:


First draw the structure of methane, then instead of four hydrogen atoms place the three phenyl groups and one -OH group to the carbon. Hence, the required structure is shown as follows:

(b) 4-(chloromethyl) heptan-3-ol:

Draw a structure containing seven carbon atoms in a long chain. Place the -OH group at the carbon atom and the chloromethyl group at the carbon atom. Hence, the required structure is drawn as follows:

(c) 2-cyclohexen-1-ol:

Draw a cyclohexane structure and place the -OH group at the carbon atom, the double bond at the  carbon atom. Hence, the required structure is drawn as follows:

(d) 3-cyclopentylhexan-3-ol:

Draw a structure containing six carbon atoms in a long chain. Now, place the -OH group and the substituent cyclopentyl group at the  carbon atom. Hence, the required structure is drawn as follows:

(e) meso-2.4-pentanediol:

Draw a structure containing five carbon atoms in a long chain. Now, place the two -OH groups at the and  carbon atoms. Hence, the required structure is drawn as follows:

(f) Cyclopentene glycol:

Draw a cyclic structure containing five carbon atoms. Place a double bond at the  carbon atom of the ring then attach the two -OH groups at the  and  carbon atom.

Hence, the required structure is shown as follows:

() 3-(iodomethyl) phenol:

Draw a phenol structure and place the iodomethyl group at the  carbon atom. Hence, the required structure is shown as follows:

(h) (2R,3R)-2,3- hexanediol:

Draw a structure containing six carbon atoms in a long chain. Place the two -OH group at the and carbon atoms with respect to the stereochemistry containing R configurations. Hence, the required structure is shown as follows:

(i) Cyclopent-3-ene-1-thiol:

Draw a cyclic structure containing five carbon atoms. Place the double bond at the carbon atom and the thiol group at the carbon atom. Hence, the required structure is shown as follows:

(j) Dimethyl disulfide:

Draw the two sulfur atoms and place the two methyl groups to the two sulfur atoms. Hence, the required structure is shown as follows:

(k) 3-methylhex-4-yn-2-ol:

Draw a structure containing six carbon atoms in a long chain. Place a triple bond at the carbon atom, -OH group at the  position and the methyl substituent at the  position. Hence, required structure is shown as follows:

Step 2 of 3

Chapter 10, Problem 33SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Draw the structures of the following compounds. (Includes