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Chapter 8
Hydroxy Functional Groups: Alcohols
35
Organic Chemistry
Undergraduate 2
10/28/2014

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Term
In systematic nomenclature, alcohols are treated as derivatives of alkanes. The ending -e of the alkane is replaced by _____
Definition
-ol
Term
In systematic nomenclature, an alkane is converted into an _____
Definition
alkanol
Term
In systematic nomenclature, the name of the alcohol is based on the longest chain that _____
Definition
contains the OH substituent
Term
In systematic nomenclature, cyclic alcohols are called _____
Definition
cycloalkanols
Term
In systematic nomenclature, when the OH group is named as a substituent, it is called _____
Definition
hydroxy
Term
In common nomenclature, the name of the alkyl group is followed by the word _____
Definition
alcohol
Term
hydrophobic
Definition
does not dissolve easily in water; ex) alkanes
Term
hydrophilic
Definition
enhances water solubility; ex) OH group, COOH, NH2
Term
Alcohols are popular _____ in the SN2 reaction due to their "water-like" structure
Definition
protic solvents
Term
To drive the equilibrium between alcohol and alkoxide (RO-) to the side of the conjugate base, it is necessary to use a base _____ than the alkoxide formed
Definition
stronger
Term
A stronger base has a _____ conjugate acid
Definition
weaker
Term
How does the addition of a halogen to an alcohol affect its acidity?
Definition
It increases the acidity by aiding in stabilizing the negative charge of the conjugate base
Term
amphoteric
Definition
molecules that may be both acids & bases
Term
Is the hydroxy functional group amphoteric?
Definition
yes
Term
synthesis gas
Definition
a pressurized mixture of CO & H2 that is used to make methanol on a multibillion-pound scale
Term
oxidation
Definition
a process that adds electronegative atoms such as halogen or oxygen to, or removes hydrogens from, a molecule
Term
reduction
Definition
the removal of halogen or oxygen or the addition of hydrogen; opposite of oxidation
Term
The reduction of aldehydes & ketones with hydride reagents is a useful way of synthesizing alcohols. This approach would be even more powerful if we could use a source of _____ instead of hydride
Definition
nucleophilic carbon
Term
What does "R:-" symbolize?
Definition
a carbon-based nucleophile
Term
organometallic reagents
Definition
the compound created when a metal acts on a haloalkane; a carbon atom of an organic group is bound to a metal
Term
Grignard reagents
Definition
organomagnesium compounds; named after the discoverer F.A. Victor Grignard
Term
carbanion
Definition
when a carbon has the negative charge in a bond
Term
reverse polarization
Definition
the preparation of alkylmetals from haloalkanes; changes which relative atoms in the molecules have the negative/positive charges
Term
Are alkanes extremely strong or weak acids?
Definition
extremely weak
Term
Are carbanions strong bases?
Definition
yes
Term
The reaction of organometallic compounds with formaldehyde results in _____
Definition
primary alcohols
Term
The reaction of organometallic compounds with aldehydes other than formaldehyde results in _____
Definition
secondary alcohols
Term
The reaction of organometallic compounds with ketones furnishes _____
Definition
tertiary alcohols
Term
total synthesis
Definition
the process of figuring out the steps needed to make a target molecule as efficiently as possible
Term
Does fluoride make a good leaving group?
Definition
NO
Term
homologation
Definition
a one-carbon extension
Term
What type of questions fall under "synthetic methodology"?
Definition
What is a good reaction? What sort of structures can we make by applying it?
Term
The best approach to the preparation of the target is to work its synthesis _____ on paper; AKA retrosynthetic analysis
Definition
backward
Term
In retrosynthetic analysis, strategic carbon-carbon bonds _____ are broken at points where bond formation seems possible
Definition
in the target
Term
What symbol is used to indicate "derives from"?
Definition
a double-shafted arrow; a "retrosynthetic arrow"
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