Aldehydes Aldehydes Ketones and Carboxylic Carboxylic Acids
Aldehydes and ketones are generally prepared by oxidation of primary and secondary alcohols respectively (Unit 11
INFRARED SPECTROSCOPY (IR)
as those found in alcohols and carboxylic acids as shown below. The following slide shows a spectrum of an aldehyde and a ketone. Study the.
5-reduction.pdf
carboxylic acids esters
Lab 14: Qualitative Organic Analysis
group (alcohol ketone
Carbonyl Chemistry (12 Lectures) Aldehydes and Ketones
alcohol to carboxylic acid: four electron oxidation aldehyde to Aldehydes and ketones react with primary amines to form imines or. Schiff bases.
testsforfunctionalgroups - inorganiccompounds
glacial acetic acid. Alcoholic compounds on reaction with ceric ammonium nitrate ... to carboxylic acids while ketones require relatively stronger.
Identifying an Unknown Compound by Solubility Functional Group
amine alkene alcohol
ethanoic acid anhydride acid chloride ester amide nitrile aldehyde
ester amide nitrile aldehyde ketone alcohol ether thiol sulfide or thioether. 1o amine ethanol. 2-methoxypropane. N. H. CH3. CH3. 2o amine. 3o amine.
Objectives Organic Chemistry 360
alcohols aldehydes
13. Carbonyl Compounds. Ketones Aldehydes
https://chem.ucr.edu/sites/g/files/rcwecm2681/files/2019-10/Chapter13.pdf
Carbonyl Chemistry (12 Lectures)
Aim of Course
•To build upon elements of Dr E.H. Smith's and Dr. D.C. Braddocks's course. •To introduce the chemistry of the carbonyl functional groups.Course Objectives
At the end of this course you should be able to:
•Identify the various functional groups that involve carbonyls •Explain reaction mechanisms associated with each type of functional groupRecommended Texts
•Vollhardt, K.P.C. & Schore N.E. "Organic Chemistry" (2nd ed.) •Clayden J., Greeves N., Warren S. & Wothers P. "Organic Chemistry" •Sykes, P. "Mechanism in Organic Chemistry" (6th ed.) •Warren, S. "Chemistry of the Carbonyl Group"Professor Donna G. Blackmond
d.blackmond@imperial.ac.uk tel. 41193 Room 639 C1 2Aldehydes and Ketones
•Aldehydes •Ketones •Carboxylic acids R C H OCarboxylic acid derivatives:
•Esters •Anhydrides •Acid halides •Amides •We begin our study of carbonyl compounds with the study of aldehydes aldehydes and ketones ketones (the aldehyde/ketone oxidation level). -Carbonyl compounds are molecules containing the carbonyl group, C=O.These include:
R C R' O R C OH O R C OR' O O C R' O R O R C NH 2 O R C X ONote: two bonds to heteroatoms
3Nomenclature of Aldehydes and Ketones
•Common names are used for the simplest aldehydes and ketones: formaldehyde butyraldehyde benzaldehyde acetone benzophenone acetophenone O C HH O C H CH 2 CH 2 CH 3 O C CH 3 H 3 C C O HC O CH 3 C O •Common names are also used for carbonyl-containing substituent groups, which are known collectively as acyl groups: HC O H 3 CC O C O formylacetyl benzoyl 4Nomenclature of Aldehydes and Ketones
•Traditional names are used for a great many aldehydes and ketones which were recognized as substances long before systems of nomenclature were developed: O H O CH O •Three of the four bases which comprise DNA contain carbonyl groups (and all four bases are nitrogen heterocycles, which we will discuss later): NH N H O O H 3 C NH N N H N O NH 2 N N H NH 2 O guanine (G)thymine (T) cytosine (C) cinnamaldehyde furfural acrolein CHC O H H 2 C 5Structure of Aldehydes and Ketones
•The carbonyl carbon of an aldehyde or ketone is sp 2 -hybridized. •The bond angle is close to 120° (trigonal planar). •The carbon-oxygen double bond consists of: -A ! C-O bond -A " C=O bondWe can compare the C=O bond length
to those of C=C double bonds 6Properties of Aldehydes and Ketones
•Aldehydes and ketones are polar molecules because the C=O bond has a dipole moment: C O •Their polarity makes aldehydes and ketones have higher boiling points than alkenes of similar molecular weight. •Aldehydes and ketones are not hydrogen bond donors (they can't donate a proton); therefore, they have lower boiling points than alcohols of similar molecular weight. •Aldehydes and ketones are hydrogen bond acceptors; this makes them have considerable solubilities in water. R C R' O H O H H O HKetones such as acetone are good solvents
because they dissolve both aqueous and organic compoundsRecall that acetone is a polar, aprotic solvent.
For acetone: dipole moment = 2.7 D
boiling piint = 56.5 ºCFor propene:dipole moment = 0.4 D
boiling point = -47.4 ºCFor i-propanol:dipole moment = 1.7 D
boiling point = 82.3 ºC 7Reactions of Aldehydes and Ketones
•The reactions of aldehydes and ketones can be divided into two main categories: -Reactions of the carbonyl group (Ch. 19) -Reactions involving the !-carbon (Ch. 22) O C C •Carbonyl group reactions fall into three main groups: -Reactions with acids -Addition reactions -Oxidation 8Carbonyl Group Reactions
•Reactions with acids: -The carbonyl oxygen is weakly basic. -Both Bronsted and Lewis acids can interact with a lone pair of electrons on the carbonyl oxygen. O C E O C E •For example, when the Bronsted acid H 3 O is used: O C H O H H O C H H O H 9Carbonyl Group Reactions
•Addition Reactions -Carbonyl groups in aldehydes and ketones undergo addition reactions. -This is one of the most important reactions of the carbonyl group. O C O C E YE Y •Addition reactions occur by two different mechanisms: -Base-catalyzed addition (under basic or neutral conditions) -Acid-catalyzed addition (under acidic conditions) •In some cases, we can carry out the same overall reaction using either set of conditions (acidic or basic). 10Carbonyl Group Reactions
•Carbonyl groups in aldehydes and ketones may be oxidized to form compounds at the next "oxidation level", that of carboxylic acids. O C H O C OH oxidation •Alcohols are oxidized to aldehydes and ketones (example: biological oxidation of ethanol to acetaldehyde) •The carbonyl group may be further oxidized to carboxylic acids H 3 CC H CH 3 OH H 3 CCCH 3 O H 3 CCOH H 3 CCOH O H H alcohol to aldehyde: two electron oxidation alcohol to carboxylic acid: four electron oxidation aldehyde to carboxylic acid: two electron oxidation H 3 CCOH O H 3 CCH O 11Basicity of Aldehydes and Ketones
•Reactions which occur at the carbonyl oxygen of aldehydes and ketones: -The weakly basic carbonyl oxygen reacts with protons or Lewis acids -The protonated form of the aldehyde or ketone is resonance-stabilized -This gives the aldehyde/ketone conjugate acid carbocation character H 3 C C CH 3 O H H 3 C C CH 3 O H + H 2 O •Protonated aldehydes and ketones can be thought of as #-hydroxy carbocations •When an alkyl group replaces (conceptually) the proton, an #-alkoxy carbocation is formed: H 3 C C CH 3 O H 3 C C CH 3 O R Rquotesdbs_dbs14.pdfusesText_20[PDF] alcohol and amine reaction
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