Tuesday 9:30 A.M, March 24th-April 13th, 2015
CEM 2820 Formal Lab Report #2- Multistep Synthesis of 5,5-Diphenylhydantoin
Objective: The objective of this experiment was to conduct the multistep synthesis
Learning Log 20.1-20.7
The carbonyl group is a very important functional group in organic chemistry, because of
its electron-deficient carbon and easily broken bond make it susceptible to a plethora of
Two broad classes of compounds contain a c
Learning Log 19.1-19.6
Carboxylic acids are organic compounds containing a carboxy group (COOH).
The C atom of a carboxy group is surround by 3 groups, making it sp2 hybridized and trigonal
planar. The C=O of a carboxylic acid is shorter than its C-O.
Learning Log 17.8-17.11
Benzene is the most common aromatic compound having a single ring. Completely
conjugated rings larger than benzene are also aromatic if they are planar and have 4n + 2
electrons. Hydrocarbons containing a single ring with alternat
Learning Log 17.1-.3, 17.5-17.7
Benzene is the simplest aromatic hydrocarbon, and has 4 degrees of unsaturation, making
it a highly unsaturated hydrocarbon, and benzene undergoes substitution reactions, not addition.
Thus, any structure proposed for benze
Learning Log 19.7-19.12
Carboxylic acids are typically prepared by oxidation reactions.
The most important reactive feature of a carboxylic acid is its polar OH bond, which is readily
cleaved with base. Carboxylic acids react as BL acids, aka: proton dono
Learning Log 15.11-15.14
Oils are susceptible to oxidation at their allylic C atoms. Oxidation occurs by way of a
radical chain mechanism:
Step 1- Oxygen in the air abstracts an allylic H atom to form an allylic radical because the allylic
CH bond is weak
Learning Log 15.1-15.6
A radical is a reactive intermediate with a single unpaired electron, formed by homolysis
of a covalent bond. A radical contains an atom that does not have an octet of electrons, making it
reactive and unstable.
Carbon radicals are
Learning Log 16.8-16.11
Four features distinguish conjugated dienes from isolated dienes.
The C-C single bond joining the two double bonds is unusually short.
Conjugated dienes are more stable than similar isolated dienes.
Some rxns of conjugated diene
Learning Log 16.1-16.7
Conjugation occurs whenever p orbitals can overlap on three or more adjacent atoms.
Two common conjugated systems are 1,3 dienes and allylic carbocations.
1,3-Dienes such as 1,3-butadiene contain two C-C double bonds joined by a sin
Learning Log 16.12-16.15
The Diels-Alder reaction is an addition reaction between a 1,3-diene and an alkene called
a dienophile, to form a new six-membered ring.
Three curved arrows are needed to show the cyclic electron movement of electron pairs
Learning Log 20.8-20.12
The most common oxidation reaction of carbonyl compounds is the oxidation of
aldehydes to carboxylic acids. A variety of oxidizing agents can be used. Aldehydes are oxidized
selectively in the presence of other functional groups us
Learning Log 21.8-21.12
Treatment of an aldehyde or a ketone with either NaBH4 or LiAlH4 followed by
protonation gives a 1 or 2 alcohol.
Treatment of an aldehyde or a ketone with either an organolithium or Grignard followed
by water gives a 1, 2 or 3 alco
Learning Log 21.13-21.17
Treatment of a carbonyl compound with water in the presence of an acid or base catalyst
adds the elements of H and OH across the C=O bond, forming a gem-diol or hydrate.
Increasing the number of alkyl groups on the carbonyl carbon
General Chemistry I
All material sort-of copyrighted, Drs. Daus, Garrett, Moore, Stace
Belmont University, 2015
Before you begin the lab experience for this semester you must sign a form indicating that you
Learning Log 25.11-25.17
Amines attack carbonyl groups to form products of nucleophilic addn or substitution.
Rxn of 1 and 2 amines with aldehydes and ketones.
Rxn of NH3 and 1 and 2 amines with acid chlorides and anhydrides.
Amines, like alcohols, contai
Learning Log 25.1-25.6
Amines are organic nitrogen compounds. Formed by replacing one or more hydrogen
atoms of ammonia with alkyl groups. The amine nitrogen atom has a nonbonded electron pair,
making it both a base and a nucleophile. Therefore, amines re
Learning Log 25.7-25.10
There are 3 types of rxns used to prepare an amine:
-Nucleophilic substitution using nitrogen nucleophiles
-Reduction of other nitrogen-containing functional groups
-Reductive amination of aldehydes and ketones
The simplest method
Learning Log 24.1-24.4
In these rxns, one carbonyl component serves as the nucleophile and one serves as the
electrophile, and a new C-C bond is formed.
The presence or absence of a leaving group on the electrophilic carbonyl carbon determines the
Learning Log 23.6-23.8
Enolates react with electrophiles to afford substitution products.
Enolates react with other carbonyl groups at the electrophilic carbonyl carbon.
Treatment of a ketone or aldehyde with halogen and either acid or base results in
Learning Log 23.1-23.5
Nucleophilic addition occurs when there is no electronegative atom Z on the carbonyl carbon.
Nucleophilic acyl substitution occurs when there is an electronegative atom Z on the carbonyl
Rxns can also occur at the alpha carb
Learning Log 22.13-22.18
Because amides have the poorest l.g out of all the carboxylic acid derivatives, they are
the least reactive. Under strenuous rxn conditions, amides are hydrolyzed in acid or base to form
carboxylic acids or carboxylate anions.
Learning Log 22.1-22.6
This chapter focuses on carbonyl compounds that contain an acyl group bonded to an
electronegative atom. These include carboxylic acids and derivatives such as acid chlorides,
anhydrides, esters and amides. Anhydrides contain two ca
Learning Log 20.13-20.17
Organometallic reagents react with carboxylic acid derivatives to form two different
products, depending on the identity of both the leaving group and the reagent. The most useful
rxns are carried out with esters and acid chloride
Learning Log 15.7-15.10
Halogenation is useful because it adds a functional group to a previously
unfunctionalized molecule, making an alkyl halide.
The stereochemistry of a rxn product depends on whether the rxn occurs at a stereogenic
center or another
Learning Log 14.1-14.10
Two common types of NMR spectroscopy are used to characterize organic structure:
-1H NMR: Used to determine the number and hype of H atoms.
-13C NMR: Used to determine the type of C atoms.
The basic source of energy in NMR is radio
Learning Log 12.12-12.15
Alcohols are oxidized to a variety of carbonyl compounds, depending on the alcohol
and the reagent. Oxidization occurs by replacing the C-H bonds on the carbon
bearing the OH group by C-O bonds.
1 alcohols are oxidized to either
Chemistry Ch. 17.4-.6
The general rules for predicting solubility of ionic compounds in water were introduced
earlier. To develop a better approach, we must start with the rules of chemical equilibrium.
Consider a saturated solution of silver chloride tha