CHEM 232 Exam 3 with Accurate Solutions

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CHEM 232 Exam 3 with Accurate Solutions

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2026/2027

Institution CHEM 232

Course CHEM 232

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CHEM 232 Exam 3 with Accurate Solutions

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CHEM 232 Exam 3 with Accurate
Solutions

aldol - ANS-Contains both aldehyde and alcohol functional groups.

ether - ANS-

alcohol -> R-X and P=O formation - ANS-PBr3, PCl3
inversion occurs
no carbocation

alcohol -> R-OMs , R-OTs , R-OSOCF3 - ANS-ClMs, ClTs, TfOTf and pyridine
no inversion
LG: Cl or OSOCF3

unhindered alkyl halide + metal alkoxide -> ether - ANS-WILLIAM ETHER SYNTHESIS
(SN2)
reagent examples: ClCH2CH3 + NaO(CH2)4CH3

OH-C's-X -> ether rings - ANS-INTRAMOLECULAR WILLIAM SYNTHESIS:
Good Nu/strong base

1.acid/base
2.ring closure 3>5>6>4>7,8

2 similarly alpha substituted alcohols -> symmetric ether - ANS-SYMMETRIC ETHER
SYNTHESIS WITH ACID:
H2SO4, H2O
1°-> SN2 + acid/base
2°, 3° -> SN1 + acid/base
less substituted alcohol: NU
more substitute alcohol: E

Ring + 1 eq H-X -> Open Ring
Open Ring + Excess H-X -> Open Ring with 2 X's - ANS-ETHER CLEAVAGE
oxonium, H-X, H2S04,
X= Br, I, Cl
1°-> SN2
2°, 3° -> SN1

, halohydrin(alcohol + x) -> epoxide - ANS-INTRAMOLECULAR WILLIAMSON:
good nu, strong base
Ring Closure

epoxide + SCH3 -> opened epoxide - ANS-BASIC CONDITIONS:
-use ether solvents
-SN2 + acidic workup (INVERSION!!!)
-attack least substituted C

epoxide + poor nu -> opened epoxide - ANS-ACIDIC CONDITIONS:
-activate O first
-lengthening bond, weakens bond-> opens backside
-SN2 + acid/base
-attack most substituted C

special nu for epoxide opening - ANS-USE ETHER SOLVENTS
LiAlH4 (hydride)
LiR, RMgBr, R-C-CNA (organometallic)

ester -> 1° alcohol - ANS-2x LiAlH4
reduction

carboxylic acid -> 1° alcohol - ANS-2x LiAlH4
reduction

aldehyde -> 1° alcohol - ANS-NaBH4 or LiAlH4
reduction

ketone -> 2° alcohol - ANS-NaBH4 or LiAlH4
reduction

HYDRIDE REDUCING: LiAlH4 - ANS--addition + acidic workup
-use ether solvents
-aldehydes/ketones -> ROH
-opens epoxides, deprotonates alcohols
-replaces halogens/sulfonate esters (SN2)
-reduces esters/carboxylic acids (SnAc -> 1° OH)

HYDRIDE REDUCING: NaBH4 - ANS--more selective, weak base, use alcohol solvents
-addition + acid/base
-aldehydes/ketones -> ROH ONLY

ester -> 3° alcohol - ANS-2x organometallic
reduction

aldehyde-> 2° alcohol - ANS-organometallic

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Uploaded on: August 1, 2026
Number of pages: 5
Written in: 2026/2027
Type: Exam (elaborations)
Contains: Questions & answers

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