Question

11. Suggest a sequence of synthetic steps through which phenylacetic acid can be prepared from toluene and in which Grignard chemistry is employed.

12. Provide the structure of cyclohexanecarbaldehyde.

13. how might one distinguish an aldehyde from a keytone using IR data alone?

15. what features are prominent in the infrared spectrum of a carboxylic acid?

16. provide the major organic product in he reaction of 3-methylpentanoic acid with CH2N2.

17. Provide the structure of (R)-4-ethoxypentanenitrile.

Provide the structure of propanoic anhydride.

Devise an efficient method for preparing 1-pentanamime from but-1-ene.

7) Provide the structure of the major organic product in the reaction below CH,CH, NaBH, CH,CH.OR 8) Provide the structure of the major organic product in the reaction below. LAAIH, (excess) CHO 9) Provide the structure of the major organic product in the reaction below. Ha (excess) Raney N Provide the structure of the major organic product in the reaction shown below. CH.CH,Mglr RT ANSWER. Write the word or phrase that best completes each statement 17) Provide the structure of (R)-4-ethoxypentanenitrile 18) Provide the major organic product of the following reaction NH acetic anhydride

Answer 1

11. substitution of bromine in the presence of light on toluene will give benzyl bromide further treat in the presence of Mg/dry ether, G.R. will be formed and it will react with CO2, PAA will be formed.

13.

Aldehyde shows doublet at around ~2700 and ~2800 cm-1 due to aldehyde -CH Fermi resonance and ketone does not give these bands.

Both gives around 1720 cm-1 abs. band for carbonyl group but ketone gives lower value.

15. Carboxylic acid shows abs. band broad 2800-3200 cm-1 due to hydrogen bobds in dimeric from and carbonyl around ~1720 cm-1.

16. 3- methyl pentanoic acid with diazomethane ester will be formed.

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O H . HO

ろ -cn- Pentanamire