Organic Chemistry ACS Exam Latest
Updated 2025 With Complete Solutions
What is anti-markovnikov? - ANSWERS-When the H adds to the carbon with the fewest
attached hydrogens
What is syn - ANSWERS-H and B add to the same face of the alkene.
What is markovnikov? - ANSWERS-Halide component of HX bonds adds to the more
highly substitued carbon, whereas the hydrogen prefers the carbon which already
contains more hydrogens.
What is aromatic sulfonation? - ANSWERS-reagent is h2so4, heat or so3 (fuming
h2so4)
What is an activating group? - ANSWERS-Ortho or para directing
What is a deactivating group? - ANSWERS-meta directing
What are examples of activating EDG? - ANSWERS-O, NR2, NH3, OH, OR, NHCOR,
OCOR, R, BENZENE, C=CR2,
What are deactivating EWG? - ANSWERS--X, COH, COR, COOR, COOH, COCL, CF3,
CN, HSO3-, NH3+ NR3+, NO2+
EDG ______ the rate of reaction - ANSWERS-increase
When naming carboxylic acids - ANSWERS-find the longest continuous carbon atom
chain contianing the carboxylic acid group
What is the prefix in carboxylic acids? - ANSWERS--oic acid
To name an ester, - ANSWERS-identify the alkyl group that is in the 'alcohol' portion of
the molecule and name it; then identify the acid part of the molecule. The ester is
named with the alkyl part first, and the acid part is named as a carboxylate.
The terms ortho, meta, and para are used when benzene derivatives possess -
ANSWERS-exact 2 subsituents
Is a structure with more or less covalent bonds more stable? - ANSWERS-More
covalent bonds is more stable
,What is the downside to separation of charges? - ANSWERS-Separation of charges
cost energy and results in a less stable resonance contributor
What does the nitrate ion look like lewis structure? - ANSWERS-
The bonding pi orbital is lower in energy than antibonding orbital (T/F)? - ANSWERS-
True
The sigma orbital is lower in energy than the pi orbital (T/F)? - ANSWERS-True
How do you prepare epoxides? - ANSWERS-Reagent is peracid (COOOH) ; alkene to
an epoxide; maintain stereochemistry
What are the reagents of hydroboration of alkenes? - ANSWERS-BH3, Et2O
EWG ________ the rate of reaction - ANSWERS-decrease
What are resonance effects? - ANSWERS-Those that occur through the pi system and
can be represented by resonance structures
What are inductive effects? - ANSWERS-Those that occur through the sigma system
due to electronegativeity type effects.
What does EDG do? - ANSWERS-Atoms adjacent to the pi system activate the
aromatic ring by increasing the electron density on the ring through a resonance
donating effect. (ortho-para directing)
What does an EWG do? - ANSWERS-EWGs with pi bonds to electronegative atoms
adjacent to the pi system deactivate the aromatic ring by decreasing the electron
density on the ring through a resonance withdrawing effect. (meta directing)
Halogens are deacitvaitng but have both - ANSWERS-inductive electron withdrawing
and resonance donating (electronegativity and lone pair donation)
What is the aldol condensation reaction? - ANSWERS-reaction in which an enol or an
enolate ion reacts with a carbonyl compound to form a beta hydroxyaldehyde or b-
hydroxyketone, followed by dehydration to give a conjugated enone.
How does one transform a fischer projection into a cyclic ring in chair conformation? -
ANSWERS-Freely rotate the bonds (change the position of the OH and CH2OH in the
fischer projection, then the oyxgen-H bond will nucleophilically attack the carbon, kick
the double bond of the oxygen to the oxygen to form an oxygen anion and then get
protonated by a hydrogen from the alcohol gorup used to nucleophilically attack the
carbon. (mechanism is in notebook)
,What reaction uses BuLi? - ANSWERS-Correy Fuches
What is the starting and end product of the Ph3P, Br- ? - ANSWERS-ketone; alkene
What is LiAlh4? - ANSWERS-A reducing agent; carboxylic acid and ester can be
reduced by this in addtiiton to aldehydes or ketones
What happens in a free-radical additon of H-Br to alkenes? (HBr RO-OR) - ANSWERS-
antiadditon or syn addition of H and Br. Antimarkovnikov.
Enolate (ester) --> ketone - ANSWERS-NaOEt --> PhCh2Br --> H3O+, heat (Remove
CO2)
What is saponification? - ANSWERS-is the alkaline hydrolysis of the fatty acid esters.
Example: The chemical reaction between any fat and sodium hydroxide is a
saponification reaction. triglyceride + sodium hydroxide (or potassium hydroxide) →
glycerol + 3 soap molecules
Carbonyl attack
What is a Grignard reagent? - ANSWERS-an organometallic chemical reaction in which
alkyl, vinyl, or aryl-magnesium halides (Grignard reagents) add to a carbonyl group in
an aldehyde or ketone. This reaction is an important tool for the formation of carbon-
carbon bonds.
How do you prepare a Grignard reagent? - ANSWERS-Treat magnesium, and then you
treat the Grignard with a strong acid. This gives you the alkane. You can also use this to
introduce deuterium (D) into molecules! The first step is to make the Grignard reagent
What's a decoupled HNMR? - ANSWERS-shows no splitting at all; it consists of a set of
single
peaks, one for each carbon or each set of equivalent carbons in a molecule. (EXAMPLE
in the exam is that benzene is basically meso, so the signals must be individual 6
signals on their own.
What are the reagents of the Claisen condensation? - ANSWERS-claisen condensation
between esters containing alpha hydrogens, promoted by a base such as sodium
thoxide, affords beta keto esters.
(use stronger bases to increase yield: NaH)
The reducing agent: NaBH4 reduces? - ANSWERS-Aldehydes and Ketones
The reducing agent: LiAlH4 reduces - ANSWERS-Carboxylic acids and esters
Why can LiAlH4 reduce more? - ANSWERS-Because the Al-H bond is weaker and thus
less stable than B-H bond.
, When using LiAlH4 to reduced amides what happens? (h2o workup) - ANSWERS-
RCH2NH2
How does one form an epoxide? - ANSWERS-From C=C to epoxide ; ring closure forms
via a intramolecular SN2 reaction.
What is the chemical properties of an epoxide? - ANSWERS-Cylic ether with a three
atom ring; ring approximates an equilateral triangle ; making it pretty reactive, more than
other ethers produced on a large scale.
What reagents are used to form an epoxide? - ANSWERS-mCPBA or a base
What is PCC in DCM? - ANSWERS-Used in oxidation of primary alcohols to aldehydes;
and oxidation of secondary alcohols to ketones ; usually used to oxidize alcohols into
carbonyl compounsd
What is the Wittig reaction? - ANSWERS-Reaction which involves the reaction of an
aldehyde or ketone; The phosphoran (PH3P= CR3R4 can be used to produce an
alkene, but then proceed to form an unstable 4 membered ring.
What happens after phosphonium ylide is added to a ketone or aldehyde? - ANSWERS-
Alkene CH2 is formed; PH3P=O by product.
What happens when MCPBA is added to an alkene? - ANSWERS-Forms into an
epoxide!!
What happens when an workup is applied to an epoxide? - ANSWERS-OH OH;
BREAKS apart the ether
Why do we use AlCl3 in Friedel Crafts- Alkylation? - ANSWERS-Good lewis acid
catalyst
What do the reagents KOH and hydrazine (NH2NH2) do? - ANSWERS-Wolff Kischner
reduction; used to convert carbonyl functionalities into methylene groups; forms R,R=N-
NH2 ; or just CH2!! The imine intermediate forms tho
What is the imine formation? - ANSWERS-Benzene ring double bonded N-NH2
What is the polymer Nylon 6,6 made from? - ANSWERS-Polyamide ; 6 long carbonyl at
each end of the chain; 4 carbons in between each of them; then 6 carbons in between
each amine group
What is the polymer polyurethane made from? - ANSWERS-Alcohol , isocyanate, and
ester like amide like thing. (RCOONHR)
Updated 2025 With Complete Solutions
What is anti-markovnikov? - ANSWERS-When the H adds to the carbon with the fewest
attached hydrogens
What is syn - ANSWERS-H and B add to the same face of the alkene.
What is markovnikov? - ANSWERS-Halide component of HX bonds adds to the more
highly substitued carbon, whereas the hydrogen prefers the carbon which already
contains more hydrogens.
What is aromatic sulfonation? - ANSWERS-reagent is h2so4, heat or so3 (fuming
h2so4)
What is an activating group? - ANSWERS-Ortho or para directing
What is a deactivating group? - ANSWERS-meta directing
What are examples of activating EDG? - ANSWERS-O, NR2, NH3, OH, OR, NHCOR,
OCOR, R, BENZENE, C=CR2,
What are deactivating EWG? - ANSWERS--X, COH, COR, COOR, COOH, COCL, CF3,
CN, HSO3-, NH3+ NR3+, NO2+
EDG ______ the rate of reaction - ANSWERS-increase
When naming carboxylic acids - ANSWERS-find the longest continuous carbon atom
chain contianing the carboxylic acid group
What is the prefix in carboxylic acids? - ANSWERS--oic acid
To name an ester, - ANSWERS-identify the alkyl group that is in the 'alcohol' portion of
the molecule and name it; then identify the acid part of the molecule. The ester is
named with the alkyl part first, and the acid part is named as a carboxylate.
The terms ortho, meta, and para are used when benzene derivatives possess -
ANSWERS-exact 2 subsituents
Is a structure with more or less covalent bonds more stable? - ANSWERS-More
covalent bonds is more stable
,What is the downside to separation of charges? - ANSWERS-Separation of charges
cost energy and results in a less stable resonance contributor
What does the nitrate ion look like lewis structure? - ANSWERS-
The bonding pi orbital is lower in energy than antibonding orbital (T/F)? - ANSWERS-
True
The sigma orbital is lower in energy than the pi orbital (T/F)? - ANSWERS-True
How do you prepare epoxides? - ANSWERS-Reagent is peracid (COOOH) ; alkene to
an epoxide; maintain stereochemistry
What are the reagents of hydroboration of alkenes? - ANSWERS-BH3, Et2O
EWG ________ the rate of reaction - ANSWERS-decrease
What are resonance effects? - ANSWERS-Those that occur through the pi system and
can be represented by resonance structures
What are inductive effects? - ANSWERS-Those that occur through the sigma system
due to electronegativeity type effects.
What does EDG do? - ANSWERS-Atoms adjacent to the pi system activate the
aromatic ring by increasing the electron density on the ring through a resonance
donating effect. (ortho-para directing)
What does an EWG do? - ANSWERS-EWGs with pi bonds to electronegative atoms
adjacent to the pi system deactivate the aromatic ring by decreasing the electron
density on the ring through a resonance withdrawing effect. (meta directing)
Halogens are deacitvaitng but have both - ANSWERS-inductive electron withdrawing
and resonance donating (electronegativity and lone pair donation)
What is the aldol condensation reaction? - ANSWERS-reaction in which an enol or an
enolate ion reacts with a carbonyl compound to form a beta hydroxyaldehyde or b-
hydroxyketone, followed by dehydration to give a conjugated enone.
How does one transform a fischer projection into a cyclic ring in chair conformation? -
ANSWERS-Freely rotate the bonds (change the position of the OH and CH2OH in the
fischer projection, then the oyxgen-H bond will nucleophilically attack the carbon, kick
the double bond of the oxygen to the oxygen to form an oxygen anion and then get
protonated by a hydrogen from the alcohol gorup used to nucleophilically attack the
carbon. (mechanism is in notebook)
,What reaction uses BuLi? - ANSWERS-Correy Fuches
What is the starting and end product of the Ph3P, Br- ? - ANSWERS-ketone; alkene
What is LiAlh4? - ANSWERS-A reducing agent; carboxylic acid and ester can be
reduced by this in addtiiton to aldehydes or ketones
What happens in a free-radical additon of H-Br to alkenes? (HBr RO-OR) - ANSWERS-
antiadditon or syn addition of H and Br. Antimarkovnikov.
Enolate (ester) --> ketone - ANSWERS-NaOEt --> PhCh2Br --> H3O+, heat (Remove
CO2)
What is saponification? - ANSWERS-is the alkaline hydrolysis of the fatty acid esters.
Example: The chemical reaction between any fat and sodium hydroxide is a
saponification reaction. triglyceride + sodium hydroxide (or potassium hydroxide) →
glycerol + 3 soap molecules
Carbonyl attack
What is a Grignard reagent? - ANSWERS-an organometallic chemical reaction in which
alkyl, vinyl, or aryl-magnesium halides (Grignard reagents) add to a carbonyl group in
an aldehyde or ketone. This reaction is an important tool for the formation of carbon-
carbon bonds.
How do you prepare a Grignard reagent? - ANSWERS-Treat magnesium, and then you
treat the Grignard with a strong acid. This gives you the alkane. You can also use this to
introduce deuterium (D) into molecules! The first step is to make the Grignard reagent
What's a decoupled HNMR? - ANSWERS-shows no splitting at all; it consists of a set of
single
peaks, one for each carbon or each set of equivalent carbons in a molecule. (EXAMPLE
in the exam is that benzene is basically meso, so the signals must be individual 6
signals on their own.
What are the reagents of the Claisen condensation? - ANSWERS-claisen condensation
between esters containing alpha hydrogens, promoted by a base such as sodium
thoxide, affords beta keto esters.
(use stronger bases to increase yield: NaH)
The reducing agent: NaBH4 reduces? - ANSWERS-Aldehydes and Ketones
The reducing agent: LiAlH4 reduces - ANSWERS-Carboxylic acids and esters
Why can LiAlH4 reduce more? - ANSWERS-Because the Al-H bond is weaker and thus
less stable than B-H bond.
, When using LiAlH4 to reduced amides what happens? (h2o workup) - ANSWERS-
RCH2NH2
How does one form an epoxide? - ANSWERS-From C=C to epoxide ; ring closure forms
via a intramolecular SN2 reaction.
What is the chemical properties of an epoxide? - ANSWERS-Cylic ether with a three
atom ring; ring approximates an equilateral triangle ; making it pretty reactive, more than
other ethers produced on a large scale.
What reagents are used to form an epoxide? - ANSWERS-mCPBA or a base
What is PCC in DCM? - ANSWERS-Used in oxidation of primary alcohols to aldehydes;
and oxidation of secondary alcohols to ketones ; usually used to oxidize alcohols into
carbonyl compounsd
What is the Wittig reaction? - ANSWERS-Reaction which involves the reaction of an
aldehyde or ketone; The phosphoran (PH3P= CR3R4 can be used to produce an
alkene, but then proceed to form an unstable 4 membered ring.
What happens after phosphonium ylide is added to a ketone or aldehyde? - ANSWERS-
Alkene CH2 is formed; PH3P=O by product.
What happens when MCPBA is added to an alkene? - ANSWERS-Forms into an
epoxide!!
What happens when an workup is applied to an epoxide? - ANSWERS-OH OH;
BREAKS apart the ether
Why do we use AlCl3 in Friedel Crafts- Alkylation? - ANSWERS-Good lewis acid
catalyst
What do the reagents KOH and hydrazine (NH2NH2) do? - ANSWERS-Wolff Kischner
reduction; used to convert carbonyl functionalities into methylene groups; forms R,R=N-
NH2 ; or just CH2!! The imine intermediate forms tho
What is the imine formation? - ANSWERS-Benzene ring double bonded N-NH2
What is the polymer Nylon 6,6 made from? - ANSWERS-Polyamide ; 6 long carbonyl at
each end of the chain; 4 carbons in between each of them; then 6 carbons in between
each amine group
What is the polymer polyurethane made from? - ANSWERS-Alcohol , isocyanate, and
ester like amide like thing. (RCOONHR)
