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29 Cards in this Set

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As far as the number of p orbitals, what is good way to interpret sp^3?
All 3 of the p orbitals have been hybridized; none remain
As far as the number of p orbitals, what is a good way to interpret sp^2?
2 of the p orbitals have been hybridized; only 1 remains.
As far as the number of p orbitals, what is a good way to interpret sp?
1 of the p orbitals ahve been hybridized; 2 remain
When a carbonyl bond breaks, (C=O), what usually happens to the electrons?
Electrons from teh pie bond end up as negative chage on the oxygen
What does the cyanide attack on hydrides usually occur in the presence of and why?
Usually occurs in the presence of acids, because the Cn- attacks the C=O crotch ~ O becomes negative and attracts H+
Show how dissolving a cyanohydrin in water can give back the aldehyde or keton you started with.
What is more favorable: ketone cyanohydrins or aldehyde cyanohydrins?
Aldehyde cyanohydrins
Why are ketone cyanohydrins less favorable than aldehyde cyanohydrins?
Aldehyde cyanohydrins are more favorable than keton cyanohydrins, because of the size of the groups attached to the carbonyl carbon atom. Aldehyde central carbon has less steric hinderance - one of the bonds coming off is to an H, (which is very small), making the reduction in angle less of a problem than than with a larger group coming off in ketone.
What is the Burgi-Dunitz trajectory?
Nucleophiles attack the plane of the carbonyl group at about 107 degrees to the C=O bond.
In terms of nucleophile attack angle, what is steric hinderance?
Portions of the molecule that get in the way of the Burgi-Dunitz trajectory
Does nucleophilc attack by H- ever happen?
Why doesn't nucleophilic attack by H- ever happen?
H- one s-orbital is too small to act as nucleophilically.
What happens instead of H- acting as a nucleophile? Draw an example.
H- acts as a base, pulling off another H from H-X, leaving X-, which then acts as the nucleophile.


Hydrogen atom is trasnferred with an attached pair of electrons'. which can still be regarded as a"'hydride transfer.

Example: B-2
What is the difference between an aldehyde and a ketone?
Both have C=O
Aldehydes have an H coming off of the central C, whereas ketones have R coming off of the central C.
Draw the reaction of lithium aluminum hydride to show why it reacts violently and dangerously with water in an exothermic reaction.
Why are organometallic reagents strong nucleophiles?
They are highly polarized toward the carbon.

Ex.: Li-C and Mg-C
Can water be present during the reaction of organometallic reagents with carbonyls?
No, because water destroys the organometallics before they have a chance to react with the carbonyls.

Ex. B-4
What are Grignard reagents?
Organomagnesium reagents that are among the most important ways of making carbon-carbon bonds.
Draw an example of a reaction involving a Grignard reagent.
Ex. B-5
Why does an aqueous solution of formaldehyde contain essentially no CH2O? Draw the reaction.
It is completely hydrated

As the equibrium constant gets larger, does the reaction shift more to the left or to the right?
The larger the equilibrium constant, the more the equilibrium is to the right.
Do cyclopropanones want a larger or smaller bond angle? Why?
Cyclopropanones prefer a smaller bond angle, because in the cyclopropanone, central carbon is sp^2, so it wants 120 degrees, whereas in cyclopropanone hydrate, the central carbon is sp^3, so it only wants 109 degrees. therefore, when cyclopropanone and cyclopropanone hydrate both get 60 degrees, the cyclopropanone hydrate is happier, becuase there is less of a difference from its ideal bond angle.

Drawn: B-7
WHa tis a hemiacetal and how is it formed?
Hemiacetal is "halfway to an acetal;" formed by an alcohol acting on a carbonyl

Ex.: B-8
Show an example of an intramolecular reaction that forms a hemiacetyl.
Ex.: B-9
In the reaction in B-10, what acts as the catalyst?
Ethanol, (EtOH)
How does an acid catalyst work for carbonyl groups?
Make the carbonyl group more electrophilic.

Illustrated in B-11.
How does a base catalyst work for carbonyl groups?
Make the nucleophile more nucleophilic.

Illustrate in B-11.
Draw a reaction involving sodium bisulfite and a ketone.
How are sodium bisulfite compounds made?
Made by mixing the ladehyde or ketone with saturated aqueous sodium bisulfit in an ice bath, shaking, and crystallizing.