Alkene-Alkyne Homework



Alkene-Alkyne Homework, CH343, Spring 2010: Due Tuesday, April 6, Noon

1. Show how the following compounds can be synthesized in high yield from the indicated starting materials, and any other reagents. All of these require a minimum of a carbon-carbon bond forming reaction, followed by a functional group transformation. Attempted one-step reactions will receive NO credit.

| |Product |Starting Material |

|a. |[pic] |[pic] |

|b. |[pic] |[pic] |

|c. |[pic] |[pic] |

|d. |[pic] |[pic] |

|e. |[pic] |[pic] |

|f. |[pic] |Starting materials that contain no more than ONE|

| | |ring. |

2. Fill in the needed reagents in the following reaction scheme. It is part of a synthesis of Longifolene, which is found in turpentine.

[pic]

3. Propose a reasonable structure for the following sets of spectra. Explain what information you obtained from each spectrum. You will obtain information from each spectrum! Label the peaks in the NMR spectra with the corresponding hydrogens and carbons in the structure.

Mass Spectrum

[pic]

IR Spectrum

[pic]

Carbon NMR Spectrum

[pic]

Proton NMR Spectrum

[pic]

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