Question

Identify and name all the compounds/conditions/catalysts (incl. the missing ones) in the
following conversions.
(a) CH2=CH2 ------?----→ CH3CH2OH ------?----→ ..............?......----?--
→ CH3COOC2H5
(b) CH3OH --------?-----→ .........?........ ------?-----→ CH3CN ---------?---
→ CH3COOH
(c) CH3CH2CH2CHO -----?--→ CH3CH2CH2CH(OH)CN ------?---→
.........?........ -----?----→ CH3CH2CH2CHBrCOOH
(d) CH3CHO ---[HCN & gentle reflux]→ .........?........ ---[HCl (aq) &
reflux]→ .........?........ ---[heat with NaBr & conc.H2SO4] →
..........?............. ---[heat with NH3 in sealed tube]→ .............?.............

Answer 1

Answer on Question #77809, Chemistry / Organic Chemistry

Question:

Identify and name all the compounds/conditions/catalysts (incl. the missing ones) in the following conversions.

Answer:

(a)

CH₂=CH₂ (ethylene) + H₂O (water, heat under pressure) → CH₃CH₂OH (ethanol)

CH₃CH₂OH (ethanol) + CuO (copper II oxide, heat) → CH₃CHO (acetaldehyde)

CH₃CHO (acetaldehyde) + Al(OC₂H₅)₃ (aluminum ethylate, catalyst, 0°C) → CH₃COOC₂H₅ (ethyl acetate)

(b)

CH₃OH (methanol) + PI₃ (phosphorus III iodide) → CH₃I (iodomethane)

CH₃I (iodomethane) + NaCN (sodium cyanide) → CH₃CN (acetonitrile)

CH₃CN (acetonitrile) + HCl(aq) (hydrochloric acid, reflux) → CH₃COOH (acetic acid)

(c)

CH₃CH₂CH₂CHO (butanal) + HCN (hydrogen cyanide, gentle reflux) → CH₃CH₂CH₂CH(OH)CN (1-cyanobutan-1-ol or butanal cyanohydrin)

CH₃CH₂CH₂CH(OH)CN (1-cyanobutan-1-ol) + HCl(aq) (hydrochloric acid, reflux) → CH₃CH₂CH₂CH(OH)COOH (2-hydroxypentanoic acid)

CH₃CH₂CH₂CH(OH)COOH (2-hydroxypentanoic acid) [heat with NaBr & conc.H₂SO₄] → CH₃CH₂CH₂CHBrCOOH (2-bromopentanoic acid)

(d)

CH₃CHO (acetaldehyde) + HCN (hydrogen cyanide, gentle reflux) → CH₃CH(OH)CN (1-hydroxypropan-1-ol or propanal cyanohydrin)

$$\begin{array}{l} \mathrm{CH_3CH(OH)CN} \quad (1\text{-hydroxypropan-1-ol}) + \mathrm{HCl(aq)} \quad (\text{hydrochloric acid, reflux}) \rightarrow \\ \mathrm{CH_3CH(OH)COOH} \quad (2\text{-hydroxypropionic acid}) \end{array}$$ \begin{array}{l} \mathrm{CH_3CH(OH)COOH} \quad (2\text{-hydroxypropionic acid}) \quad [\text{heat with NaBr \& conc. H_2SO_4}] \rightarrow \\ \mathrm{CH_3CHBrCOOH} \quad (2\text{-bromopropionic acid}) \end{array} \begin{array}{l} \mathrm{CH_3CHBrCOOH} \quad (2\text{-bromopropionic acid}) \quad [\text{heat with NH_3 in sealed tube}] \rightarrow \\ \mathrm{CH_3CH(NH_2)COOH} \quad (2\text{-aminopropionic acid}) \end{array}