Download Organic Chemistry Midterm Review Go over the Activities and

Organic Chemistry Midterm Review
Go over the Activities and Chapter Tests. Review the problems on WileyPlus.
Chapter 1: Covalent Bonding and Shapes of Molecules
1.
2.
3.
4.
5.
Write the ground-state electron configuration for nitrogen
Which is more electronegative: Carbon or Nitrogen
Chlorine or Bromine
Write a Lewis structure for Hydrazine, N2H4 Polar/Nonpolar?
Write a Lewis structure for carbonate ion.
Write the Lewis structure and assign formal charges for :
6. Arrange the single covalent bonds in order of increasing polarity: C—H, O—H, N—H
7. Be able to identify bond angles and hybridization ie. Ethyl alcohol
8. Tetrafluoroethylene, is the starting material for the synthesis of the polymer
poly(tetrafluoroethylene), commonly known as Teflon. Propose a structure. Write LDS,
predict molecular polarity ( identify with δ+ or δ-) and type of hybridized orbitals and
bond angles.
9. Draw resonance structures for the following:
10. Review functional groups
Chapter 2: Acids and Bases
11. Complete the net ionic equation.
12. Used curved arrows to show the flow of electron in the reaction: HCO3− + OH− →
13. Choose the most acidic protons:
14. Choose the strongest acid: Nicotinic acid (niacin, Ka 1.4 × 10−5) or acetylsalicylic acid
(aspirin, Ka 3.3 × 10−4)
15. Arrange in order of increasing base strength:
16. Complete equations for the Lewis Acid-Lewis base pairs. Use curved arrows to show
the flow of electrons during the reaction.
17. Be able to predict where equilibrium will lie:
**For an acid–base reaction, one way to indicate the predominant species at equilibrium is to say that
the reaction arrow points to the acid with the higher value of pKa.
Chapter 3: Alkanes and Cycloalkanes
18. Write a line angle formula for the following:
19. Write a condensed structural formula:
20. Each member of the following set of compounds is an alcohol; that is, each contains an —OH
(hydroxyl group). Which structural formulas represent (1) the same compound, (2) different
compounds that are constitutional isomers, or (3) different compounds that are not constitutional
isomers?
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
21. Draw line-angle formulas for
(a)The four alcohols with the molecular formula C4H10O.
(b)The two aldehydes with the molecular formula C4H8O.
(c)The one ketone with the molecular formula C4H8O.
(d)The three ketones with the molecular formula C5H10O.
(e)The four carboxylic acids with the molecular formula C5H10O2.
22. Write a line angle formula for: trans-1,3-Dimethylcyclopentane
23. The following is the structure of Germacrene A, a hydrocarbon synthesized in plants and
studied for its insecticidal properties. Classify each of the sp3 hybridized carbons as 1°, 2°, 3°,
or 4°.
24. Which of the following conformations are more stable and explain.
25. Draw both chair forms and indicate the more stable one.
26. Draw alternative chair conformations and indicate the more stable one.
27. Dodecane, C12H26, is an unbranched alkane. Predict the following:
(a)Will it dissolve in water?
(b)Will it dissolve in hexane?
(c)Will it burn when ignited?
(d)Is it a liquid, solid, or gas at room temperature and atmospheric pressure?
(e)Is it more or less dense than water?
Chapter 4: Alkenes and Alkynes
28. Predict bond angles for the following and identify the sigma and pi bonds and the
hybridization :
29. Draw a structural formula for :
3-Ethyl-3-methyl–1-pentyne
trans -1,2-Diisopropylcyclopropane
30. Which of these alkenes show cis–trans isomerism? For each that does, draw structural
formulas for both isomers.
(a)1-Hexene
(b)2-Hexene
(c)3-Hexene
(d)2-Methyl–2-hexene
(e)3-Methyl–2-hexene
(f)2,3-Dimethyl–2-hexene
31. Arrange the groups in each set in order of increasing priority:
(a)—CH3, —Br, —CH2CH3
(b)—OCH3, —CH(CH3)2, —CH2CH2NH2
(c)—CH2OH, —COOH, —OH
(d)—CH CH2, —CH
O, —CH(CH3)2
32. Determine whether the structures in each set represent the same molecule, cis–trans isomers,
or constitutional isomers. If they are the same molecule, determine whether they are in the
same or different conformations as a result of rotation about a carbon–carbon single bond.
(a)
(b)
(c)
(d)
Chapter 11: IR
Be able to read IR ( given frequencies of functional groups) and determine the identity of the
compound
Mass Spec
Be able to read a simple mass spectrum. Be able to identify the base peak, M+ peak, determine if
Br is present or Cl is present.
20 Answer:
1.Compounds (a) and (g) represent the same compound.
Compounds (d) and (e) represent the same compound.
2.Compounds (a = g), (d = e), and (f) represent constitutional isomers of C4H10O.
Compounds (b) and (c) represent constitutional isomers of C4H8O.
3.The isomers of C4H10O [(a = g) and (d = e)] are different compounds from the isomers of C4H8O
[(b) and (c)], and all are different from compound (h).
23.
26.
27. Answer:
(a)No
(b)Yes
(c)Yes
(d)liquid
(e)less dense
29. trans
30.
Answer:
(b)
(c)
(e)
31. Answer:
(a)—CH3 < —CH2CH3 < —Br
(b)—CH2CH2NH2 < —CH(CH3)2 < —OCH3
(c)—CH2OH < —COOH < —OH
(d)—CH(CH3)2 < —CH
CH2 < —CH
O