CHEM 3305 – Organic Chemistry I Session #28: 12/3/2024 🎄

SI Leader: Om Bhakta Tuesday Finals Test Prep

Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

Objectives Covered: Exam Dates:

• Chapter 10 & 11 Questions - September 24th ✅
• Practice Final Exam - October 22nd ✅
• Resources & Study Tips - November 19th ✅
• Reaction Summaries & Flashcards - December 5th 🕒 (<2 days)
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“And in case I don’t see you, good afternoon, good evening and good night!”
- Truman Burbank; The Truman Show (1998)

This document is property of Texas Tech and cannot be reproduced or disseminated. Dissemination or
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CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

Announcements:
Walk-In Hours: Wednesday 12/4 from 2-5 PM at TTU Library Basement
Final Exam for Dr. Mayer’s MWF Section: Thursday 12/5 10:30 AM - 1:00 PM in MCOM 067

End of Semester Survey:

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CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

Ch. 10 & 11 Practice Questions

HI

Draw the mechanism.

H 2O
cat. H2SO4

Draw the mechanism.

Br2
CH2Cl2

Draw the mechanism.

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CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
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1) BH3, THF
2) H2O2, KOH

Br2

CH3OH

excess HCl
-80°C

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CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

1) BH3 ⋅ THF
2) H2O2, OH-

H2O

H2SO4, HgSO4

1) NaH
2) C(CH3)3I

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CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

OH
1) POCl3, pyridine
2) Br2, CH2Cl2
3) 2 equiv NaNH2, 2 equiv H

Devise a synthesis for the following reaction. There are five steps to this reaction. Make sure to include
the proper reagents. Hint: Find out what type of reactions make your product and then work backwards.

HO

product reactant

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reproduction of this property will result in a referral to the Office of Student Conduct.
CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

Mock Exam:
1. Among the following anions, which one could not exist (to any significant extent) in tert-butyl
alcohol? The structure for tert-butyl alcohol is shown.

A) H2PO4 - C) CN -
B) NH2 - D) HCO2 - OH
tert-butyl alcohol
(CH3)3COH

2. Which of the following species is least likely to act as a Bronsted-Lowry Acid? Note: There is more
than one answer.

A) H2O B) KOH C) H3PO4 D) LiH E) CH3SO3H

3. Which of the following species would act as the second weakest conjugate acid?

F O O
O Cl O

O O
O O
Cl F Cl
F

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CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

4. Of the four groups in the structure shown below, which is the second-most basic? Which group would
form the most acidic conjugate acid?

O
O
S

O
N

5. Draw the products of the following reaction. Label the acid, base, conjugate acid, and conjugate base.
Then determine which side of the reaction equilibrium favors.

H3O + NH2

6. Which of the following structures has the ability to hydrogen bond to a water molecule, but not
hydrogen bond to another of the same structure?

OH NH2 OH

O
O OH

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CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

7. Which of the following structures has the highest boiling point?

A) O O B) HO OH

C) D) HO
OH OH

8. Rank the following structures from highest melting point to lowest melting point.

Cl Cl Cl Cl

Cl Cl Cl

Cl Cl

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CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

9. Which of these molecules best corresponds to the mass spectrum below?

A) C) Br

Cl
B) D)
NH2

10. Below is the mass spectrum for 3-ethylpentane. What is the peak with an m/z = 71 called?

A) M+ peak
B) M + 1 peak
C) Base peak
D) Fragment peak

10

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reproduction of this property will result in a referral to the Office of Student Conduct.
CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

11. Which of the following spectrums is produced by the IR spectrum?

O OH
A) C)
O O

OH

B) D)
O
OH

12. Which of these molecules best corresponds to the IR spectrum below?

A) C)

NH
B) D)
N

11

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reproduction of this property will result in a referral to the Office of Student Conduct.
 CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

13. Draw the following Newman projections for the given molecule with the perspective shown.

HO

OH

The lowest energy staggered conformation The highest energy staggered conformation The highest energy eclipsed conformation

14. Draw the highest stability chair conformation for the following cyclohexane. Afterwards, perform a
ring flip of the conformation.

12

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reproduction of this property will result in a referral to the Office of Student Conduct.
CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

15. Rank the following Newman Projections in order of increasing energy.

CH3 H H
H3C CH2CH3 H3C CH2CH3 H CH3

H H H3C H H3C H
H H CH2CH3
I. II. III.

16. How many of the structures shown below are meso?

NH2
PH2
F

H2P HO OH
F NH2

17. How many of the structures shown below are optically active?

13

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reproduction of this property will result in a referral to the Office of Student Conduct.
CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

18. If the excess of enantiomer Z in the following solution is 80%, what is the total % of each
enantiomer?

Enantiomer Z

19. What is the relationship between the following two structures?

A) Enantiomers
Br
B) Diastereomers OH
C) Constitutional Isomers OH
D) Identical
Br

20. What is the relationship between the following two structures?

A) Enantiomers
OCH3
OH
B) Diastereomers
HO
C) Constitutional Isomers
D) Identical OCH3 Br

Br

14

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reproduction of this property will result in a referral to the Office of Student Conduct.
CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

Thank you for a fantastic semester! I thoroughly enjoyed helping you all getting through Organic
Chemistry 1 and it has been a pleasure to do so. Best of luck on your final and all future endeavors that
come your way. If you have any questions, feel free to reach out! And of course, Happy Holidays!
- Om

Resources & Study Tips:

1. The Organic Chemistry Tutor (YouTube

2. Implement active recall by completing practice problems after reviewing a concept and make
flashcards (Anki, electronic, or handmade)

3. Complete practice problems and after reviewing which you got incorrect, go back, and watch
the videos recommended.

4. Make a list of muddy topics so you know what to emphasize when you study

5. Plan how you will study (I like using Notion and Google Calendar to help me plan ahead)

6. You can rent study spaces at the library - https://www.depts.ttu.edu/library/studySpaces/

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reproduction of this property will result in a referral to the Office of Student Conduct.
 CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

Substrate Protic Solvent Aprotic Solvent Strong Base Bulky Base

H2O, CH3OH, EtOH DMF, DMSO, I-. CN- OH-, CH3O-, EtO-
O

Methyl Halide SN2 SN2 SN2 SN2

1° Halide SN2 SN2 SN2 & E2 E2

2° Halide SN1 & E1 SN2 SN2 & E2 (major) E2

3° Halide SN1 & E1 SN1 & E1 E2 E2

Alkenes & Alkynes: https://quizlet.com/974304509/reactions-of-alkenes-and-alkynes-flash-

cards/?i=67xztp&x=1jqt
SN2, SN1, E2, E1: https://quizlet.com/846742704/chem-3305-substitution-elimination-flash-cards/?i=67xztp&x=1jqt
Alcohols, Ethers, and Epoxides: https://quizlet.com/971807094/organic-chemistry-reactions-with-alcohols-ethers-and-
epoxides-flash-cards/?i=67xztp&x=1jqt

16

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reproduction of this property will result in a referral to the Office of Student Conduct.
CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

17

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CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

18

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reproduction of this property will result in a referral to the Office of Student Conduct.
CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

19

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reproduction of this property will result in a referral to the Office of Student Conduct.
 CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

1. Hydrohalogenation - Forms alkyl halides (Addition of H-X)

R Mixture of syn and anti products

R X R X
formed
H HX H H
R R + Follows Markovnikov’s Rule
R
H H
Forms carbocation intermediate
H H H
(Rearrangements may occur)

2. Hydration - Forms alcohols or ethers (Addition of H2O or ROH)

R R OH R OH
Occurs under acidic conditions
H H 2O H H
R R
+ R Mixture of syn and anti products
H2SO4 H H
formed
H H H
Follows Markovnikov’s Rule
Forms carbocation intermediate
R R OR R OR (Rearrangements may occur)
H ROH H H
R R
+ R
H2SO4 H H

H H H

3. Halogenation - Forms vicinal dihalides (Addition of X2)

Only occurs with Cl2 or Br2

H H X
Solvents included CCl4 or
H X
CH2Cl2
R X2 R R
R R + R
Favors anti products formed
solvent

H X H X
No Markovnikov’s Rule Applied
H
Forms a cyclic halonium
intermediate

20

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reproduction of this property will result in a referral to the Office of Student Conduct.
 CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

4. Halohydrin Formation - Forms a halohydrin or haloether

X can be Cl2, Br2, NBS or NCS

H H X H X
Occurs with H2O and protic solvents

R R R
OH bonds to most substituted C, X
X2
R R + R
bonds to least substituted C
H2O

H OH H OH
Favors anti products formed
H
Forms a cyclic halonium
intermediate

5. Hydroboration Oxidation - Forms alcohols

Occurs with BH3 or B2H6

R Follows Anti-Markovnikov’s Rule

H R H R

R R
Favors syn products formed
1) BH3 R
R R + R
2) H2O2, OH- First step is a concerted addition of
H OH H
borane on least substituted C
H OH
Second step is the oxidation of BH2
to OH

6. Hydrohalogenation - Forms geminal dihalides (Addition of 2 H-X)

X X X = Cl, Br, or I
Follows Markovnikov’s Rule
2 equiv HX H
R H
R Forms carbocation intermediate
(No rearrangements)
H H

X X H H

2 equiv HX R R
R R
R
+
R

H H X X

21

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reproduction of this property will result in a referral to the Office of Student Conduct.
 CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

7. Halogenation - Forms tetrahalide product (Addition of 2 X2)

X = Cl, Br, or I
X X
No Markovnikov Selectivity
2 equiv X2 H
R H
R
Forms bridged-ion intermediate
After 1st equiv, a trans dihalide is
X X
formed

X X X X

2 equiv X2 R R
R R
R R

X X X X

8. Hydration - Forms a ketone (Addition of H2O with H2SO4 or HgSO4 catalyst)

First step is Markovnikov Addition of

O
H2O to form an enol
H2O H Enol undergoes tautomerization to form
R H
H2SO4 or HgSO4 R a ketone
H H Equilibrium favors ketones over enols

O H H

H2O R R
R R + R
H2SO4 or HgSO4 R

H H O

22

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reproduction of this property will result in a referral to the Office of Student Conduct.
 CHEM 3305 – Organic Chemistry I Session #28: 12/3/24 🎄
SI Leader: Om Bhakta Tuesday Finals Test Prep
Email: [email protected] 7:00 – 8:30 PM SCI 007
______________________________________________________________________________

9. Hydroboration Oxidation - Forms alcohols Occurs with BH3, R2BH, or 9-BBN

Follows Anti-Markovnikov’s Rule
H
1) BH3 R Terminal Alkynes à Aldehydes
R H
2) H2O2, NaOH, H2O
O Internal Alkynes make Ketones
First step is a concerted addition of
borane on least substituted C
R O Second step is the oxidation of BH2
1) BH3 R
R R + to OH
2) H2O2, NaOH, H2O R
O R Third step is the tautomerization of
the enol into a carbonyl

10. Converting alkynes into acetylides (good bases) which are very good for SN2 reactions.

O
HO
1 equiv NaNH2 C
H3C C CH H3C C C
H2O

23

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