
Concept explainers
a)

Interpretation:
Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how 1-ethylcyclohexanol can be prepared is to be stated.
Concept introduction:
An alicyclic 30 alcohol is to be prepared from benzene. For this purpose benzene has to be converted into an alicyclic
To state:
Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how to prepare 1-ethylcyclohexanol.
b)

Interpretation:
Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how 3-methylhexan-1-ol can be prepared is to be given.
Concept introduction:
A six carbon straight chain alcohol with a methyl group on C3 is to be prepared from benzene. By ozonolysis, the benzene ring is broken to get the open chain dialdehyde glyoxal. To one of the aldehydic group in glyoxal, an isopentyl group can be introduced by treating with a suitable Grignard reagent. Upon heating the alcohol will eliminate water to yield an unsaturated
To give:
Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how to prepare 3-methylhexan-1-ol.
c)

Interpretation:
Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how 2-methyl-2-phenyl-2 butanol can be prepared is to be given.
Concept introduction:
An
To give:
Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how to prepare .
d)

Interpretation:
Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how 5-methylhexan-3-ol can be prepared is to be given.
Concept introduction:
A six carbon straight chain aldehyde with a methyl group on C4 is to be prepared from benzene. By ozonolysis, the benzene ring is broken to get the open chain dialdehyde, maloaldehyde with three carbon atoms. To one of the aldehydic group in the dialdehyde, an isobutyl group can be introduced by treating with a suitable Grignard reagent to get an aldol. The aldehyde group in the aldol is reduced to an alkyl group to get the alcohol requireds.
To give:
Starting with benzene and using other alcohols of six or fewer carbons as the organic reagents how to prepare 3-methylhexan-1-ol.

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Chapter 17 Solutions
Organic Chemistry - With Access (Custom)
- (c) (4pts) Mechanism: heat (E1) CH3OH + 1.5pts each _E1 _ (1pt) Br CH3OH (d) (4pts) Mechanism: SN1 (1pt) (e) (3pts) 1111 I H 10 Ill!! H LDA THF (solvent) Mechanism: E2 (1pt) NC (f) Bri!!!!! CH3 NaCN (3pts) acetone Mechanism: SN2 (1pt) (SN1) -OCH3 OCH3 1.5pts each 2pts for either product 1pt if incorrect stereochemistry H Br (g) “,、 (3pts) H CH3OH +21 Mechanism: SN2 (1pt) H CH3 2pts 1pt if incorrect stereochemistry H 2pts 1pt if incorrect stereochemistryarrow_forwardA mixture of butyl acrylate and 4'-chloropropiophenone has been taken for proton NMR analysis. Based on this proton NMR, determine the relative percentage of each compound in the mixturearrow_forwardQ5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R Harrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
