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Suggest the most appropriate method for each of the

Chapter 3, Problem 6P

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QUESTION:

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.


(a) butan-1-ol  butanal, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CHO}\)

(b) but-2-en-1-ol  but- 2 -enoic acid, \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}-\mathrm{COOH}\)

(c) butan-2-ol  butan-2-one, \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{3}\)


(d) cyclopentanol
 1-ethylcyclopentanol (two steps)


(e) cyclopentylmethanol
 1-cyclopentylpropan-1-ol (two steps)


(f) 1 -methylcyclohexanol
 2-methylcyclohexanone (several steps)

Equation Transcription:

Text Transcription:

CH_{3}CH_{2}CH_{2}CHO

CH_{3}CH=CH-COOH

CH_{3}COCH_2CH_3

Questions & Answers

QUESTION:

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.


(a) butan-1-ol  butanal, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CHO}\)

(b) but-2-en-1-ol  but- 2 -enoic acid, \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}-\mathrm{COOH}\)

(c) butan-2-ol  butan-2-one, \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{3}\)


(d) cyclopentanol
 1-ethylcyclopentanol (two steps)


(e) cyclopentylmethanol
 1-cyclopentylpropan-1-ol (two steps)


(f) 1 -methylcyclohexanol
 2-methylcyclohexanone (several steps)

Equation Transcription:

Text Transcription:

CH_{3}CH_{2}CH_{2}CHO

CH_{3}CH=CH-COOH

CH_{3}COCH_2CH_3

ANSWER:

Solution 6P

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