Welcome Fall 05 class

A few notes for those of you taking this course fully online in the Fall of 2005.

1) Class announcements will be made to this blog.
2) Subscribe to the blog by clicking on the Subscribe with Bloglines button at the top of the blog.
3) Quizzes and tests are in WebCT. For now all students must login as guest to http://webct.drexel.edu. If you don't have the password email me. Do not go through one.drexel.edu until I let you know that it is ready.
4) The first test will be around week 5. That will show up in WebCT when it is set up through one.drexel.edu

list of student blogs

Here is the list of blogs generated by students for the extra credit assignment. The idea was to find an application of 2 reaction that we learned about in class. Most of the blogs were submitted right before the deadline so there was no time to give feedback. There are errors in many of these and several do not adhere to the guidelines (especially linking to online peer-reviewed articles). However they are listed here to highlight the multiple uses of organic synthesis and the interesting variety in the ways of presenting such information on blogs.

Akshay's Orgo Blog
Priyaabraham
Sandhyamanivannanorgo
Smitha's blog
Gwen1000
JaspreetOrgo
Jennifer's Blog
Andu's Blog
Hydroxylamine Sri
J.D.'s blog

Lecture 028: Wheel of orgo 5

There were no questions for the exam so we did one last Wheel of Orgo to practice reactions from the whole course. There were 3 enol reaction patterns to identify in the first 2 syntheses. Then we synthesized a cat from glycine.

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Lecture 028 pdf

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Lecture 027: make-up test 2 review

We went over some common mistakes made in test 2, mainly on enol chemistry.

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Lecture 027 pdf

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Lecture 026: Extra Credit Help

Here are directions for completing the extra credit for this class. In the screencast I show how to:
1) Download ChemSketch (only for Drexel students)
2) Use wikipedia and Google scholar to find an article with a relevant synthetic step.
3) Draw out the single step reaction with ChemSketch.
4) Use Paint to convert the ChemSketch work into a bitmap file.
5) Create a Flickr account to upload the bitmap file and create a tag. (Everyone in my classes use at least the "orgo" tag in Flickr.)
6) Find the url referencing the picture in Flickr using properties and insert into a blog post. (I also go through creating a Blogger account)
7) Give a brief description of the reaction and link to at least one peer-reviewed article.

Notice that all the services are completely free. A freeware version of Chemsketch is available here. I don't know how it compares to the Drexel version.

The example I used was the last step in the synthesis of ibuprofen - the hydrolysis of a nitrile. This is what it looks like.

Remember the last day to have the extra credit work done is Friday June 3, 2005 at midnight.

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There is no pdf for this lecture.

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Lecture 025: test 2 review

I gave the solutions to the extra enol problems I posted on Monday and answered questions about the test.

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Lecture 025 pdf

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Lecture 024: prob 12 d-h

We finished problem 12 on enol chemistry and completed the list of the patterns to look for in these syntheses. At the end of class I put up a few more problems of varying difficulty then assisted students in small groups. I'll post the solution to these on Wednesday.

The test will be available Wednesday afternoon, a little earlier because Sunday and Monday Korman is closed. I will answer questions on Wednesday concerning the test then if there is any time left we'll do another Wheel of Orgo. Online students make sure to email me your questions.

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Lecture 024

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Lecture 023: problem 12 a-d

We did some enol chemistry synthesis problems. If you are having trouble with this section make sure to see me after class or schedule an appointment so I can see how you are approaching the problems.

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Lecture 023 pdf

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Lecture 022: Wheel of Orgo 4

Another round of Wheel of Orgo. This time Sri won. All of the syntheses were designed to practice enol reactions.

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Lecture 022 pdf

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Lecture 021: rest of prob 11

We finished problem 11 (j-p) on enol reactions. It was a mix of Claisen condensations, malonate ester and acetoacetate ester syntheses. The last problem was an example of a Robinson annulation.

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Lecture 021 pdf

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Lecture 020: Wheel of Orgo 3

We played another Wheel of Orgo with the target products vanillin, TNT and DEET.
Mihir won this one.

I reduced the resolution of the Flash presentation to 800x600 so you don't need to scroll if you are running you desktop at 1024x768. For all prior lectures, you can avoid scrolling by increasing the resolution of your screen.

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Lecture 020 pdf

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Lecture 019: prob 11

We covered most of problem 11 about enol reactions.
We will resume Wheel of Orgo on Friday.

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Lecture 019 pdf

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Lecture 018: Wheel of Orgo II

We played "Wheel of Orgo" again today, with the modification that I only counted a point for reactions only if they were correct. Again 3 points for completing the synthesis. We did 2 relatively simple syntheses then started one difficult one (vanillin). We didn't get the chance to finish that one so we'll resume next time. Again Sujeet ended up with the most points at the end.

I would encourage you to think of ways of finishing this synthesis with the reactions we have learned. It is a good way of consolidating the material in this class. You don't need to participate, you can pass your turn and you can join the game in progress.

If you are taking the class online and would like to participate in a future Wheel of Orgo session email me so that I can plan future sessions.

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Lecture 018 pdf

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Lecture 017: Review for Test 1 Make-up

Review from email questions, class questions and the questions most wrongly answered from test 1.

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Lecture 017 pdf

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Lecture 016: problems 8-10

Carboxylic Acids and Derivatives problems done today. Remember to email me your questions for the pre-makeup review session on Wednesday.

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Lecture 016 pdf

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Lecture 015: Wheel of Orgo

We played "Wheel of Orgo" today, which is basically a review session based on a game format. Students who participated drew a single step for a synthesis on the tablet PC during their turn. One point for the step, one point for correcting a mistake in a step and 3 points for completing the synthesis. Congrats to today's winner Sujeet!

If you are taking the class online and would like to participate in a future Wheel of Orgo session email me so that I can plan future sessions.

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Lecture 015 pdf

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Lecture 014: review for test 1

In this review session I tried to show how to practice the class material by coming up with multiple syntheses for the same target molecules. If you are not coming to class make sure to email me your questions.

At the start of the session I explained how to access older items in the blog using the post links. You can also just scroll down.

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Lecture 014 pdf

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checklist for test

I noticed that the covered material section in the syllabus was outdated so I just updated it to reflect what we actually covered in class in the proper order.

Lecture 013: enols part 2

We looked at the second part of the enol section. This included Claisen condensation between esters and the crossed Claisen condensation between 2 different esters or between ketones and esters. Other synthetic strategies included the malonate ester and acetoacetic acid syntheses. Finally, Michael addition was covered.

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Lecture 013 pdf

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Lecture 012: Enols part 1

We looked at enol reactions including alpha substitution with halogens, the haloform reaction aldol condensations. Variations on the aldol condensation such as crossed and intramolecular were covered. The detailed mechanism of acid and base catalyzed aldol was presented.

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Lecture 012 pdf

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Lecture 011: Carboxylic Acids and their derivatives

We looked at carboxylic acids and their derivatives in terms of nomenclature, synthesis and reactions.

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Lecture 011 pdf

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Lecture 010: solution to problems 5 - 7

Problems 5, 6 and 7 covered amines.

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Lecture 010 pdf

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Lecture 009: Solutions to probs 3 - 4

Problems 3 and 4 covered aldehydes and ketones.

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Lecture 009 pdf

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Question about imines

Q:
Today in lecture, you were showing us how an amine can react to form
an imine by reacting with a carbonyl compound and acid. You also said
that the imine can be hydrolyzed back to the amine and carbonyl
compound by adding aqueous acid. One of the products of the reaction
you showed us today was water, so does that water and the acid thats
already present hydrolyze the imine back to the amine and ketone to
some extent to form an equilibrium? Also, is there a way to minimize
the hydrolysis back to the amine and ketone and keep the imine?

A:
Yes, it is an equilibrium. If you remove water you can drive the formation of the imine. Water can be removed using molecular sieves or distillation, depending on the reactants.

Lecture 008: Amines

We looked at amines - nomenclature, reactions and preparation.

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Lecture 008 pdf

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Lecture 007: Ketone Reactions

We looked at ketone and aldehyde reactions.

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Lecture 007 pdf

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Lecture 006: Problem 002 and Ketone Preparation

Here are the solutions to synthesis problem 002 on aromatics. We also covered the rest of the preparation methods for aldehydes and ketones.

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Lecture 006 pdf

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Lecture 005: Solutions to Problem 001

Here are the solutions to problem 001 on aromatics.

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Lecture 005 pdf

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Lecture 004: Benzyne, Aldehydes and Ketones - preparation

We finished up aromatics looking at the benzyne mechanism, side-chain oxidation with permanganate and a review of a few reactions like free radical halogenation and elimination at the side chain. Reviewed the nomenclature of ketones and aldehydes and listed methods of their preparation.

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Lecture 004 pdf

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Problem set

Here are the first questions of the Problem Set.

1) Predict the products from the reaction of toluene, nitrobenzene and m-chlorotoluene with:
a) 1-chloropropane/AlCl3
b) KMnO4 (hot, concentrated)
c) HNO3/H2SO4
d) HNO3/I2
e) AlI3/I2
f) t-butanol/BF3
g) SO3/H2SO4
h) Br2/light
i) PhCOCl/AlCl3
j) NaNH2
k) Br2/FeBr3
l) NaOH, 350C

2) Propose a synthesis of the following from benzene:
a) n-propylbenzene
b) m-chloronitrobenzene
c) p-iodoanisole
d) o-methylaniline
e) 1-bromo-1-phenylethane
f) methylcyclohexane

3) Predict the products from the reaction of benzaldehyde with:
a) Na2Cr2O7/H2SO4
b) KMnO4
c) PhMgBr then H3O+
d) CH3CH=PPh3
e) Ethylene glycol, H2SO4
f) HCN then H3O+,heat
g) NH2OH, H+
h) Acetone dimethyl ketal
i) NaBH4
j) NaBH3CN
k) NaBH3CN/isopropyl amine

4) Propose the synthesis of:
a) methyl ethyl ketone from 1,3-dithiane
b) benzaldehyde from toluene
c) acetophenone from ethynylbenzene
d) benzophenone from cyanobenzene
e) acetone from acetic acid
f) propionaldehyde from CH3CH2COCl
g) 2-hydroxybutanoic acid from propanoic acid

5) Predict the products from the reaction of 2-aminobutane with
a) methyl bromide (excess)
b) methyl bromide (excess) then Ag2O then heat
c) diethylamine/NaBH3CN
d) bromobenzene
e) benzoyl chloride then LiAlH4

6) Predict the products from the reaction of aniline with
a) NaNO2/HCl then H3O+
b) NaNO2/HCl then CuBr
c) NaNO2/HCl then CuCl
d) NaNO2/HCl then CuF
e) NaNO2/HCl then HBF4
f) NaNO2/HCl then H3PO2
g) Br2/FeBr3

7) Propose a synthesis of:
a) diethylmethylamine from ethylamine
b) phenylisopropylamine from benzene and acetone
c) meta-bromofluorobenzene from benzene
d) benzylamine from toluene
e) methylamine from CH3CONH2
f) 1-amino-2-phenylethane from benzylbromide
g) p-nitroaniline from aniline

8) Predict the products from the reaction of propanoic acid with:
a) LiAlH4
b) NaOH
c) acetyl chloride
d) CH3MgBr

9) Propose a synthesis of:
a) propanoic acid from 1-propanol
b) propanoic acid from ethanol
c) acetic acid from 2-pentyne
d) CH3NHCH2CH3 from acetic acid
e) CH3COOCH2CH3 from acetic acid
f) Acetic anhydride from ethanol
g) Acetophenone from an organocuprate

10) Draw the mechanisms for the formation of an amide from ammonia and CH3COOCH2CH3

11) Predict the products from the reaction of:
a) cyclohexanone with Br2(one equivalent)/CH3COOH
b) acetophenone with I2(excess)/NaOH
c) propanal with NaOH
d) 2-butanone with benzaldehyde(excess), H2SO4/heat
e) propanal with formaldehyde(excess), H2SO4/heat
f) 2,7-octanedione with NaOH/heat
g) 2,6-octanedione with H2SO4/heat
h) 2,5-octanedione with NaOH/heat
i) 2,4-octanedione with NaOH/heat
j) CH3CO2Et with NaOH
k) CH3CO2Et with NaOEt
l) CH3CO2Et with benzaldehyde(excess), NaOEt
m) CH3CO2Et with oxalic acid (HO2CCO2H) (excess), NaOEt
n) Diethyl malonate with 1) NaOEt 2) benzyl bromide 3) H3O+
o) Ethyl acetoacetate with 1) NaOEt 2) n-propyl bromide 3) H3O+
p) Cyclohexanone with 1) NaOH/methyl vinyl ketone/heat

12) Using an enolate reaction propose a synthesis of:
a) bromoacetone
b) methyl vinyl ketone
c) PhCH2CH2COCH3
d) PhCH2CH2COOH
e) PhCOCH2COOEt
f) PhCOCH2COPh
g) CH3CH(OH)CH2CHO
h) CHCl3

Lecture 003: Ortho Meta Para

We first covered a few more electrophilic aromatic substitution reactions such as nitration, sulfonation and Friedel-Crafts acylation. The advantage of using acylation followed by a Clemmensen reduction over Friedel-Crafts acylation was discussed. Hydrogenation of the aromatic ring was briefly looked at. Most of the lecture involved accounting for ortho/para and meta directing groups, as well as activating and deactivating effects.

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Lecture 003 pdf

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quizzes, tests and problem set

The first quiz is now available. The rest of the quizzes and problem set will be made available in the next few days. The first test will be around week 5.

Lecture 002: Electrophilic Aromatic Substitution

We briefly reviewed some nomenclature for aromatics then discussed the Electrophilic Aromatic Substitution mechanism. Two examples of reactions using this mechanism were discussed: Friedel-Crafts and aromatic halogenation reactions.

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Transcript

Lecture 002 pdf

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Lecture 001 Syllabus

We went over the syllabus and FAQ for the course today. I also demonstrated how to subscribe to the class podcast and to Bloglines.

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syllabus

ORGANIC CHEMISTRY
CHEM 243

Course goals and objectives: This is an introductory course to organic chemistry. Detailed mechanisms of several reactions will be covered. Course requirements are CHEM 241 and CHEM 242.

Textbook: Wade (Organic Chemistry, Ed. 5) is recommended.

Grading:
2 1.5-hour exams 2 x 100
final 200
total 400

Course Information: An FAQ for the class is maintained on this blog and is updated periodically. E-mail the instructor if your question is not addressed in the FAQ.

Make-up test policy: Tests, quizzes and exam will be available on WebCT. Location and times of testing are specified in the FAQ. Quizzes will be available for each chapter but will not count towards the final grade. Make-up tests will be available on WebCT but will consist of additional questions without additional time. The better score between the test and make-up will be used.

Lecture archives: This class can be taken fully online. The class archives are made available by screencasting as streaming audio/video as well as podcast by audio with pdfs to follow along. Students attending the class fully online are encouraged to contact the instructor by e-mail to ask questions or to schedule phone or physical appointments to go over any material that requires further explanation.

Grading Policy: A: 90-100% B: 80-89% C: 65-79% D: 50-64% F: 0-50% (borderline grades are left to the discretion of the professor)

Extra Credit: Up to 1% extra credit is available for students who create blogs discussing real world applications of the reactions we discuss in class. References must be used with at least 2 examples for full credit. Students may not use a reference already used by another student. Students may also use their blog to report on this class in general (i.e. study tips, difficulty of certain material, additional online resources found, etc.) Blogs can easily be created at http://www.blogger.com/. Since blogs are public, students do not have to use their real names but can if they choose. A list of RSS feeds to the class blogs will be made available on this blog. The deadline for completion of the two examples is the last day of classes. However, students are encouraged to post as early as possible to make use of feedback from instructor. Revisions of the posts based on feedback from the instructor (or other students) is acceptable up to the last day of classes.

Material Covered

Aromatic compounds
Electrophilic Aromatic Substitution
Mechanism: sigma complex, electrophile
-bromination of benzene with Br2 and FeBr3
-chlorination of benzene with Cl2 and AlCl3
-iodination of benzene with I2 and HNO3
-nitration of benzene with HNO3 and H2SO4
-sulfonation of benzene with SO3 and H2SO4
-Friedel-Crafts alkylation with R-X and AlCl3 or FeBr3
-Friedel-Crafts alkylation with alkenes or alcohols and acids
-Friedel-Crafts acylation with RCOCl and AlCl3 (acylium ion)

Ortho/Para directors
-Ortho directors: R, X, OR, OH, NH2, NHCOR
-Meta directors: COR, CO2H, CO2R, SO3H, CN, NO2, N+R3
-Mechanism of ortho/para direction: Resonance

Reactions at side chains
-Clemmensen reduction of Ar-COR with Zn(Hg)/HCl(aq.)
-free radical halogenation
-permanganate oxidation of ArR to ArCO2H
-SN1 substitution at benzylic halides

Other reactions
-The Benzyne mechanism: reaction of p-bromotoluene with NH2-
-Catalytic hydrogenation of aromatic ring


Ketones and Aldehydes
Carbonyl compounds:
-ketones, aldehydes, carboxylic acids, acid chlorides, esters, amides
-dipole moment
-nomenclature: formaldehyde, acetaldehyde, acetone, benzaldehyde, methyl ethyl ketone, benzophenone, acetophenone, formic acid, acetic acid, propionic acid, butyric acid, benzoic acid
-hydrogen bonding with alcohols
-infrared spectra: ketones and aldehydes 1710 cm-1

Preparation:
-secondary alcohols to ketones with Na2Cr2O7/H2SO4
-primary alcohols to acids with Na2Cr2O7/H2SO4
-primary alcohols to aldehydes with PCC
-ozonolysis of alkenes to aldehydes and ketones
-phenyl ketones from Friedel-Crafts reaction
-hydration of alkynes to ketones with Hg2+/H2SO4/H2O (Markovnikov addition)
-hydroboration-oxidation of alkynes to aldehydes with Sia2BH/H2O2, NaOH
-alkylation of 1,3-dithiane followed by hydrolysis with HgCl2 to ketones and aldehydes
-Grignard reagents and nitriles to ketones and aldehydes
-acid chlorides to aldehydes with LiAlH(O-t-Bu)3
-acid chlorides to ketones with R2CuLi

Reactions:
-nucleophilic addition of:
-Grignard reagents to alcohols
-Wittig reaction to alkenes
-hydrates and acetals – use as protecting group
-cyanohydrins then to a-hydroxy acid
-imines
-oximes and hydrazones
-oxidation of aldehydes to acids with Na2Cr2O7/H2SO4
-reduction of ketones and aldehydes with NaBH4 or LiAlH4 to alcohols

Amines
Nomenclature
-primary, secondary, tertiary, quaternary
-aniline, N,N-diethylaniline, 3-ethylaniline, p-toluidine, pyrrole, pyrrolidine, imidazole, pyridine, piperidine

Reactions
-alkylation
-acylation
-imine formation
-diazotation
-Hofmann elimination

Synthesis
-reductive amination
-acylation then reduction
-reduction of nitro compounds
-reduction of azides
-reduction of nitriles (b-hydroxy amines)
-Hofmann rearrangement

Carboxylic Acids and derivatives
Nomenclature
-formic, acetic, propionic, butyric, valeric acids, cyclohexanecarboxylica acid, benzoic acid, phthalic acids, alpha and beta
-effect of substituents on acidity

Synthesis
-from primary alcohols with KMnO4
-from alkenes or alkynes with KMnO4
-carboxylation of Grignard reagents
-hydrolysis of nitriles
Nucleophilic Acyl Substitution
-acyl halides, anhydrides, esters, amides; reactivity and preparation
-acid catalyzed and base catalyzed mechanisms for the hydrolysis of esters (tetrahedral intemediate)

Reactions
-reduction of acids and esters to primary alcohols with LiAlH4
-reduction of amides to amines with LiAlH4
-reduction of acid chlorides to aldehydes using LiAlH(O-t-Bu)3
-formation of amides from amines and acid chlorides
-formation of esters from alcohols and acid chlorides
-formation of acids from water and acid chlorides
-formation of anhydrides from acids and acid chlorides
-formation of ketones from organocuprates and acid chlorides (Grignards give alcohols)

Enols and Enolate Ions
-Mechanism of alpha substitution (base and acid catalyzed)
-the haloform reaction
-aldol condensation (base and acid catalyzed)
-dehydration of aldol products
-aldol cyclizations
-Claisen condensation
-malonic ester synthesis
-acetoacetic ester synthesis
-Michael addition