Chapter 5: Q.50 (page 208)
Draw the structure of (S)-citalopram, a drug used to treat depression and anxiety that is much more potent than its R enantiomer.
citalopram
Short Answer
The structure of the (S)-citalopram is as follows:
Chapter 5: Q.50 (page 208)
Draw the structure of (S)-citalopram, a drug used to treat depression and anxiety that is much more potent than its R enantiomer.
citalopram
The structure of the (S)-citalopram is as follows:
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a.
b.
c.
d.
Drawn are four isomeric dimethylcyclopropanes.
a. How are the compounds in each pair related (enantiomers, diastereomers, constitutional isomers): A and B; A and C; B and C; C and D?
b. Label each compound as chiral or achiral.
c. Which compounds, alone, would be optically active?
d. Which compounds have a plane of symmetry?
e. How do the boiling points of the compounds in each pair compare: A and B; B and C; C and D?
f. Which of the compounds are meso compounds?
g. Would an equal mixture of compounds C and D be optically active? What about an equal mixture of B and C?
Cellulose is water insoluble, despite its many OH groups. Considering its three-dimensional structure, why do you think this is so?
Consider Newman projections (AโD) for four-carbon carbohydrates. How is each pairof compounds related: (a) A and B; (b) A and C; (c) A and D; (d) C and D? Choose fromidentical molecules, enantiomers, or diastereomers.
A sulfonium ion (R3S+) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an R or S designation to sulfur, the lone pair is always assigned the lowest priority (4). SAM, S-adenosylmethionine, is a biologically active sulfonium ion that we will learn about in Section 7.16. Locate all the stereogenic centers in SAM, and assign an R,S designation to each center.
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