ORGANIC CHEMISTRY ACS EXAM SET 2024
COMPREHENSIVE QUESTIONS AND ANSWERS LATEST
2024
1. When naming carboxylic acids: find the longest continuous carbon atom chain
containing the carboxylic acid group
2. What is the prefix in carboxylic acids?: -oate
3. To name an ester,: 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.
4. The terms ortho, meta, and para are used when benzene derivatives possess:
exact 2 substituents
5. Is a structure with more or less covalent bonds more stable?: More covalent bonds
is more stable
6. What is the downside to the separation of charges?: Separation of charges cost
energy and results in a less stable resonance contributor 7. What does the nitrate ion
look like Lewis structure?:
8. The bonding pi orbital is lower in energy than antibonding orbital (T/F)?: True
9. The sigma orbital is lower in energy than the pi orbital (T/F)?: True
10. How do you prepare epoxides?: Reagent is peracid (COOOH) ; alkene to an
epoxide; maintain stereochemistry
11. What are the reagents of hydroboration of alkenes?: BH3, Et2O
12. What is anti-Markovnikov?: When the H adds to the carbon with the fewest
attached hydrogens
,13. What is syn: H and B add to the same face of the alkene?
14. What is markovnikov?: Halide component of HX bonds adds to the more highly
substituted carbon, whereas hydrogen prefers the carbon which already contains
more hydrogens.
15. What is aromatic sulfonation?: reagent is h2so4, heat or so3 (fuming h2so4)
16. What is an activating group?: Ortho or para directing
17. What is a deactivating group?: meta directing
18. What are examples of activating EDG?: O, NR2, NH3, OH, OR, NHCOR,
OCOR, R, BENZENE, C=CR2,
19. What are deactivating EWG?: -X, COH, COR, COOR, COOH, COCL, CF3,
CN, HSO3-, NH3+ NR3+, NO2+
20. EDG ______ the rate of reaction: increase
21. EWG ________ the rate of reaction: decrease
22. What are resonance effects?: Those that occur through the pi system and can be
represented by resonance structures
23. What are inductive effects?: Those that occur through the sigma system due to
electronegativeity type effects.
24. What does EDG do?: 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)
25. What does an EWG do?: 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)
26. Halogens are deactivating but have both: inductive electron withdrawing and
resonance donating (electronegativity and lone pair donation)
27. What is the aldol condensation reaction?: 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.
28. How does one transform a fischer projection into a cyclic ring in chair
conformation?: 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)
29. What reaction uses BuLi?: Correy Fuches
, 30. What is the starting and end product of the Ph3P, Br- ?: ketone; alkene
31. What is LiAlh4?: A reducing agent; carboxylic acid and ester can be reduced by
this in addtiiton to aldehydes or ketones
32. What happens in a free-radical additon of H-Br to alkenes? (HBr RO-OR):
antiadditon or syn addition of H and Br. Antimarkovnikov.
33. Enolate (ester) --> ketone: NaOEt --> PhCh2Br --> H3O+, heat (Remove CO2)
34. What is saponification?: 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
35. What is a Grignard reagent?: 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.
36. How do you prepare a Grignard reagent?: 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
37. What's a decoupled HNMR?: 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.
38. What are the reagents of the Claisen condensation?: 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)
39. The reducing agent: NaBH4 reduces?: Aldehydes and Ketones
40. The reducing agent: LiAlH4 reduces: Carboxylic acids and esters
41. Why can LiAlH4 reduce more?: Because the Al-H bond is weaker and thus less
stable than B-H bond.
42. When using LiAlH4 to reduced amides what happens? (h2o workup): -
RCH2NH2
43. How does one form an epoxide?: From C=C to epoxide ; ring closure forms via a
intramolecular SN2 reaction.
44. What is the chemical properties of an epoxide?: 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.
45. What reagents are used to form an epoxide?: mCPBA or a base
COMPREHENSIVE QUESTIONS AND ANSWERS LATEST
2024
1. When naming carboxylic acids: find the longest continuous carbon atom chain
containing the carboxylic acid group
2. What is the prefix in carboxylic acids?: -oate
3. To name an ester,: 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.
4. The terms ortho, meta, and para are used when benzene derivatives possess:
exact 2 substituents
5. Is a structure with more or less covalent bonds more stable?: More covalent bonds
is more stable
6. What is the downside to the separation of charges?: Separation of charges cost
energy and results in a less stable resonance contributor 7. What does the nitrate ion
look like Lewis structure?:
8. The bonding pi orbital is lower in energy than antibonding orbital (T/F)?: True
9. The sigma orbital is lower in energy than the pi orbital (T/F)?: True
10. How do you prepare epoxides?: Reagent is peracid (COOOH) ; alkene to an
epoxide; maintain stereochemistry
11. What are the reagents of hydroboration of alkenes?: BH3, Et2O
12. What is anti-Markovnikov?: When the H adds to the carbon with the fewest
attached hydrogens
,13. What is syn: H and B add to the same face of the alkene?
14. What is markovnikov?: Halide component of HX bonds adds to the more highly
substituted carbon, whereas hydrogen prefers the carbon which already contains
more hydrogens.
15. What is aromatic sulfonation?: reagent is h2so4, heat or so3 (fuming h2so4)
16. What is an activating group?: Ortho or para directing
17. What is a deactivating group?: meta directing
18. What are examples of activating EDG?: O, NR2, NH3, OH, OR, NHCOR,
OCOR, R, BENZENE, C=CR2,
19. What are deactivating EWG?: -X, COH, COR, COOR, COOH, COCL, CF3,
CN, HSO3-, NH3+ NR3+, NO2+
20. EDG ______ the rate of reaction: increase
21. EWG ________ the rate of reaction: decrease
22. What are resonance effects?: Those that occur through the pi system and can be
represented by resonance structures
23. What are inductive effects?: Those that occur through the sigma system due to
electronegativeity type effects.
24. What does EDG do?: 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)
25. What does an EWG do?: 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)
26. Halogens are deactivating but have both: inductive electron withdrawing and
resonance donating (electronegativity and lone pair donation)
27. What is the aldol condensation reaction?: 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.
28. How does one transform a fischer projection into a cyclic ring in chair
conformation?: 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)
29. What reaction uses BuLi?: Correy Fuches
, 30. What is the starting and end product of the Ph3P, Br- ?: ketone; alkene
31. What is LiAlh4?: A reducing agent; carboxylic acid and ester can be reduced by
this in addtiiton to aldehydes or ketones
32. What happens in a free-radical additon of H-Br to alkenes? (HBr RO-OR):
antiadditon or syn addition of H and Br. Antimarkovnikov.
33. Enolate (ester) --> ketone: NaOEt --> PhCh2Br --> H3O+, heat (Remove CO2)
34. What is saponification?: 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
35. What is a Grignard reagent?: 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.
36. How do you prepare a Grignard reagent?: 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
37. What's a decoupled HNMR?: 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.
38. What are the reagents of the Claisen condensation?: 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)
39. The reducing agent: NaBH4 reduces?: Aldehydes and Ketones
40. The reducing agent: LiAlH4 reduces: Carboxylic acids and esters
41. Why can LiAlH4 reduce more?: Because the Al-H bond is weaker and thus less
stable than B-H bond.
42. When using LiAlH4 to reduced amides what happens? (h2o workup): -
RCH2NH2
43. How does one form an epoxide?: From C=C to epoxide ; ring closure forms via a
intramolecular SN2 reaction.
44. What is the chemical properties of an epoxide?: 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.
45. What reagents are used to form an epoxide?: mCPBA or a base
