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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 group

Recommended 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 2

Aldehydes and Ketones

•Aldehydes •Ketones •Carboxylic acids R C H O

Carboxylic 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 O

Note: two bonds to heteroatoms

Nomenclature 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 4

Nomenclature 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 5

Structure 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 bond

We can compare the C=O bond length

to those of C=C double bonds 6

Properties 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 H

Ketones such as acetone are good solvents

because they dissolve both aqueous and organic compounds

Recall that acetone is a polar, aprotic solvent.

For acetone: dipole moment = 2.7 D

boiling piint = 56.5 ºC

For propene:dipole moment = 0.4 D

boiling point = -47.4 ºC

For i-propanol:dipole moment = 1.7 D

boiling point = 82.3 ºC 7

Reactions 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 8

Carbonyl 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 9

Carbonyl 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). 10

Carbonyl 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 11

Basicity 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 Cquotesdbs_dbs21.pdfusesText_27

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