b. Discuss the mechanism for any two of the reactions shown in Figure 4. Include all curly arrows, as well as any relevant stereochemistry considerations in your answer. (i) (ii) (iii) H Ph Br OH NaCN HO HCI MeOH NEt3 C4H7NO + NaCl A H₂SO4 catalyst C8H8O2 + Br B ✪ HNEt3 C7H1402 + H₂O C

b. Discuss the mechanism for any two of the reactions shown in Figure 4. Include all curly arrows, as well as any relevant stereochemistry considerations in your answer. (i) (ii) (iii) H Ph Br OH NaCN HO HCI MeOH NEt3 C4H7NO + NaCl A H₂SO4 catalyst C8H8O2 + Br B ✪ HNEt3 C7H1402 + H₂O C

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations

Section11.SE: Something Extra

Problem 54AP

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Question

CH2023 Q2 (b)

b.
Discuss the mechanism for any two of the reactions shown in Figure 4. Include
all curly arrows, as well as any relevant stereochemistry considerations in your
answer.
(i)
(ii)
(iii)
H
Ph Br
OH
NaCN
HO
HCI
MeOH
NEt3
C4H7NO + NaCl
A
H₂SO4 catalyst
C8H8O2 + Br
B
✪
HNEt3
C7H1402 + H₂O
C

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Step 2: A) Propanal reacting with NaCN in HCl to give propylcyanihydrine

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Step 3: B) Phenylbromide reacting with methanol using triethylamine to give ester formation (methyl phenyl e

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Step 4: C) Ethanoic acid reacting with 4-methylpentanol to give ester formation:

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