Chapter 5 - Stereochemistry Flashcards


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1
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Determine the relationship between the following two compounds? Also name the compounds according to IUPAC rules.

Diastereomers

(cis)-1,2-dimethylcyclohexane

(trans)-1,2-dimethylcyclohexane

2
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How are the compounds in each pair related to each other?

A and B are enantiomers

C and D are diasteromers

E and F are identical

G and H are constitutional isomers

3
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Determine which of the following compounds are achiral. If not, identify the stereogenic centers and label as R or S configuration.

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A and B are achiral.

4
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Determine which of the following compounds are optically active.

Compounds B and D are chiral, therefore optically active

5
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Compare the following boiling points for compounds B and D

The boiling points for the two compounds are the same.

6
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Determine which of the following molecules are chiral. If so, identify either R or S configuration.

I (R) and II (R) are chiral molecules.

7
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How many 1H and 13C NMR signals does the following compound have?

6 and 7 respectively

8
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Determine the integration and splitting pattern for each proton signal.

A - (1H) quartet

B - (9H) singlet

C - (3H) doublet

D - (3H) singlet

9
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How many 1H and 13C NMR signals does the following compound have? Determine the integration and splitting pattern for each proton signal.

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4 and 5 respectively.

10
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What information could be deduced from this IR Spectrum?

O-H group (strong broad peak around 3000)

11
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What information could be deduced from this IR Spectrum?

O-H Group (strong broad peak around 3000) and C=0 (strong peak at 1700)

12
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Which structure is most consistent with the following 1H NMR and which details allowed you to eliminate the other structures?

Structure B

A- The most downfield structure is a quartet, but the proton signal bonded directly to the oxygen is a singlet

C- There are three signals shown on the NMR whereas the structure has four signals

D- The signal on the NMR are more downfield than the protons shown on the compound