UMBC Organic Chemistry Exam 1 Study Notes

Exam Structure

  • Department: UMBC Department of Chemistry and Biochemistry

  • Course: Chem 351, Organic Chemistry I

  • Date: September 24, 2025

  • Exam Parts:

    • Part I: 20 multiple choice questions (total 60 points)

    • Must mark answers on Akindi bubble sheet

    • Only one best answer per question

    • Part II: Four free response questions (total 40 points)

    • Directions must be followed strictly for full credit

    • Answers must fit in the provided space

    • Additional page for scratch work (not graded)

Periodic Table Reference

  • Element Symbols and Atomic Numbers:

    • H (1), He (2), Li (3), Be (4), B (5), C (6), N (7), O (8), F (9), Ne (10)

    • Na (11), Mg (12), Al (13), Si (14), P (15), S (16), Cl (17), Ar (18)

    • K (19), Ca (20), Sc (21), Ti (22), V (23), Cr (24), Mn (25), Fe (26)

    • Co (27), Ni (28), Cu (29), Zn (30), Ga (31), Ge (32), As (33), Se (34)

    • Br (35), Kr (36), Rb (37), Sr (38), Y (39), Zr (40), Nb (41), Mo (42)

    • Tc (43), Ru (44), Rh (45), Pd (46), Ag (47), Cd (48), In (49), Sn (50)

    • Sb (51), Te (52), I (53), Xe (54)

    • Cs (55), Ba (56), La (57), Ce (58), Pr (59), Nd (60), Pm (61), Sm (62)

    • Eu (63), Gd (64), Tb (65), Dy (66), Ho (67), Er (68), Tm (69), Yb (70), Lu (71)

    • Ac (89), Th (90), Pa (91), U (92), Np (93), Pu (94), Am (95), Cm (96)

    • Bk (97), Cf (98), Es (99), Fm (100), Md (101), No (102), Lr (103)

Part I: Multiple Choice Questions

  1. Answer Sheet Instructions

    • Ensure name is written in the top right corner

    • Double-check bubbling of Campus ID (2 letters, 5 numbers)

    • Confirm exam version

  2. Sample Questions

    • Question 1: How many hydrogens are implied by this bond-line structure?

      • a) 9

      • b) 10

      • c) 11

      • d) 12

    • Question 2: What orbitals overlap to make the indicated bond in Zoloft?

      • a) sp3-sp2

      • b) sp3-p

      • c) sp2-sp2

      • d) sp2-p

    • Question 3: Which molecule has a molecular dipole?

      • a) 1 only

      • b) 3 only

      • c) 1 & 3

      • d) 1 & 2 & 3

    • Question 4: Number of constitutional isomers for C4H8O with carbon-oxygen double bond?

      • a) 0

      • b) 1

      • c) 2

      • d) 3

    • Question 5: Which side of acid-base equilibrium is favored?

      • a) Left, reactants more stable

      • b) Right, products more stable

      • c) Left, reactants less stable

      • d) Right, products less stable

    • Question 6: Is ethanol (CH3CH2OH) an appropriate solvent for a reaction?

      • a) Yes, unlikely to react with the base

      • b) Yes, likely to react with the base

      • c) No, unlikely to react with the base

      • d) No, likely to react with the base

    • Question 7: Rank the following hydrogens in order of increasing acidity.

    • Question 8: Role of amine in a reaction?

    • Question 9: Relationship between two given structures?

    • Question 10: Identify total lone pairs and delocalized lone pairs in a molecule.

    • Question 11: Negative charge nitrogen in resonance structure?

    • Question 12: Identify functional groups in tetrahydrogestrinone.

    • Question 13: Orbital containing aniline lone pair?

    • Question 14: Common name for substituent named as (1-methylpropyl)?

    • Question 15: Correct IUPAC naming for a shown compound?

    • Question 16: Energy cost calculations concerning H-H and H-CH3 interactions in butane.

    • Question 17: Relationship between new structures?

    • Question 18: Assign cis and trans configurations for the compounds shown.

    • Question 19: Most stable conformation of trans-1-tert-butyl-2-methylcyclohexane?

Part II: Free Response Questions

  1. Constitutional Isomers for C3H9N

    • Task: Draw all constitutional isomers using bond-line structures.

  2. DBU and HCl Reaction

    • a) Add unwritten lone pairs on DBU.

    • b) Determine the more basic nitrogen and illustrate reaction with HCl using curved arrows.

    • c) Draw the conjugate acid, including all lone pairs and formal charges.

    • d) Brief explanation of why chosen nitrogen is more basic.

  3. Resonance Structures

    • Task: Draw all reasonable resonance structures for provided species using proper curved arrows, showing all formal charges.

  4. Chair Conformation Flip

    • Task: Draw flipped chair conformation of dimethylsubstituted cyclohexane and bond-line structure using wedge and dotted lines.

Additional Notes

  • Important Reminder: Ensure all answers are original work and demonstrate understanding of concepts clearly for grading.