Discuss primary, secondary or tertiary designation if appropriate. (10 pts. each

Question

Discuss primary, secondary or tertiary designation if appropriate. (10 pts. each unknown) IR analysis of unknowns. Identify major peaks from both spectra including any peaks that may support the functional group identity. (10 pts. each) 4. NMR spectra with complete interpretation of peaks for both unknowns. Discuss integration of peaks, chemical shifts and splitting. (15 pts. each (there are 4 spectra total two H NMR and two 13C NMR.)) 5. Mass spec interpretation including molecular weight and important fragments. Detail how these fragments confirm your structure. DRAW out the fragments that correspond to the peaks. (15 pts. each) 6. A drawn structure for each unknown. You have been given the molar mass of your unknowns and the info that all alkyl halides are the bromine version. All unknowns contain only one functional group (so none contain both an alkene and an alcohol). Draw a structure for your unknown that conforms to all available data. (10 pts. each) 7. Conclusions: Write a brief conclusion that explains why you drew the unknown structures you did. Be sure to include any qualitative test data that helped you interpret your unknown structure. (10 pts. each) 8. Awanes, Awenes, small OH, large alcohol, alla halides,ether- Soivbu H20 Solubil insolvbe A) simall alconol e)etner H2 So A) Alvenu )larqealcoho i Alaiuanes icyt hatcles115

Explanation / Answer

Interpretation of spectra

4. IR shows peaks

2850-2950 cm-1 for aliphatic C-H stretch

1400-1500 cm-1 peaks for C-X stretch

5. 1H NMR

0.8 ppm (doublet, 6H) for two CH3's next to CH

2.25 ppm (nonet, 1H) for CH between two CH3's and a CH2

3.3 ppm (doublet, 2H) for CH2 between CH and a Br

6. Mass

M+ 136

Two peaks m/z 136 and m/z 138 in 1 : 1 ratio sugests presence of Br-79 and Br-81 isotopes

loss of Br gives m/z 57

7. The structure of compound would be thus,

(CH3)2CHCH2Br

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