Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 5, Problem 52P

Tartaric acid [ H O 2 C C H ( O H ) C H ( O H ) C O 2 H ] was an important compound in the history of stereochemistry. Two naturally occurring forms of tartaric acid arc optically inactive. One optically inactive form has a melting point of 210-212 °C, the ocher a melting point of 140°C. The Inactive tartaric acid with a melting point of 210-212°C can be separated into two optically active forms of tartaric acid with the same melting point (16S-170°C). One optically active tartaric acid has [ α ] D 25 = + 12 , and the other, [ α ] D 25 = 12 . All attempts to separate the other inactive tartaric acid (melting point 140°C) into optically active compounds fail.

(a) Write the three-dimensional structure of the tartaric acid with melting point 140°C.

(b) Write structures for the optically active tartaric acids with melting points of 168-170°C.

(c) Can you determine from the formulas which tartaric acid in (b) has a positive rotation and which has a negative rotation?

(d) What is the nature of the form of tartaric acid with a melting point of 210-212°C?

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Chapter 5 Solutions

Organic Chemistry

Ch. 5 - Practice Problem 5.11 List the substituents in...Ch. 5 - Prob. 12PPCh. 5 - Practice Problem 5.13 Tell whether the two...Ch. 5 - Prob. 14PPCh. 5 - Prob. 15PPCh. 5 - Prob. 16PPCh. 5 - Prob. 17PPCh. 5 - Prob. 18PPCh. 5 - Prob. 19PPCh. 5 - Prob. 20PPCh. 5 - Practice Problem 5.21 The following are formulas...Ch. 5 - Practice Problem 5.22 Write three-dimensional...Ch. 5 - Prob. 23PPCh. 5 - Practice Problem 5.24 Give names chat include (R)...Ch. 5 - Prob. 25PPCh. 5 - Prob. 26PPCh. 5 - Prob. 27PPCh. 5 - Prob. 28PPCh. 5 - Practice Problem 5.29 Write formulas for all of...Ch. 5 - Prob. 30PPCh. 5 - Prob. 31PPCh. 5 - Prob. 32PPCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - 5.35 Designate the (R) or (S) configuration at...Ch. 5 - Prob. 36PCh. 5 - (a) Write the structure of...Ch. 5 - Shown below are Newman projection formulas for...Ch. 5 - 5.39 Write appropriate structural formulas...Ch. 5 - Discuss whether each of the following compounds...Ch. 5 - Prob. 42PCh. 5 - Prob. 43PCh. 5 - Compound F has the molecular formula C5H8 and is...Ch. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - For the following molecule, draw its enantiomer as...Ch. 5 - 5.49 (Use models to solve this...Ch. 5 - 5.50 (Use models to solve this...Ch. 5 - (Use models co solve this problem.) Write...Ch. 5 - 5.52 Tartaric acid was an important compound in...Ch. 5 - Prob. 53PCh. 5 - Prob. 54PCh. 5 - Prob. 55PCh. 5 - Prob. 1LGPCh. 5 - Prob. 2LGPCh. 5 - Prob. 3LGPCh. 5 - Prob. 2QCh. 5 - Prob. 3QCh. 5 - Prob. 4QCh. 5 - Select the words that best describe what happens...Ch. 5 - Prob. 6QCh. 5 - Prob. 7QCh. 5 - Prob. 8QCh. 5 - 5.9 Which is untrue about the following...Ch. 5 - Prob. 10Q
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