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Different Chemical Bond in , Exercises of Organic Chemistry

Covalant Bond,Hydrocarbons and Oxygen-Containing Compounds.

Typology: Exercises

2021/2022

Uploaded on 02/11/2022

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Organic Chemistry Questions
The Covalent Bond
1. The hybridization of the central carbon in CH3CN and the bond angle CCN are
a. sp2, 180°.
b. sp, 180°.
c. sp2, 120°.
d. sp3, 109°.
2. Which of the following statements about an sp hybridized carbon is FALSE?
a. It is divalent.
b. It forms bonds that are linear.
c. It has two p orbitals.
d. It always forms triple bonds to carbon.
3. Which molecule has the largest dipole moment?
a. HCl
b. CCl4
c. H2S
d. CO2
4. What are the hybridizations of carbons 1 and 2 respectively in the following structure?
a. sp3 and sp2
b. sp2 and sp3
c. sp3 and sp
d. sp2 and sp2
pf3
pf4
pf5
pf8
pf9
pfa
pfd
pfe
pff
pf12
pf13
pf14
pf15
pf16
pf17
pf18
pf19
pf1a
pf1b
pf1c
pf1d
pf1e
pf1f
pf20
pf21
pf22
pf23
pf24
pf25
pf26
pf27
pf28
pf29
pf2a
pf2b
pf2c
pf2d
pf2e
pf2f

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Organic Chemistry Questions

The Covalent Bond

  1. The hybridization of the central carbon in CH 3 C≡N and the bond angle CCN are

a. sp^2 , 180°. b. sp , 180°. c. sp^2 , 120°. d. sp^3 , 109°.

  1. Which of the following statements about an sp hybridized carbon is FALSE?

a. It is divalent. b. It forms bonds that are linear. c. It has two p orbitals. d. It always forms triple bonds to carbon.

  1. Which molecule has the largest dipole moment?

a. HCl b. CCl (^4) c. H 2 S d. CO 2

  1. What are the hybridizations of carbons 1 and 2 respectively in the following structure?

a. sp^3 and sp^2 b. sp^2 and sp^3 c. sp^3 and sp d. sp^2 and sp^2

  1. What are the hybridizations of atoms 1 and 2 respectively in the following structure?

a. sp^3 and sp^2 b. sp^2 and sp^3 c. sp^3 and sp d. sp^2 and sp^2

  1. Identify the orbital hybridization at the two indicated carbons in the molecule below.

a. C^1 : sp ; C^2 : sp b. C^1 : sp^2 ; C^2 : sp^2 c. C^1 : sp ; C^2 : sp^2 d. C^1 : sp^2 ; C^2 : sp

  1. How many total resonance structures can be drawn for the following anion (include those without separation of charge)?

a. 1 b. 2 c. 3 d. 4

  1. What is the specific rotation 20[α ]D of the following molecule?

a. +4.42 o b. +0.442 o c. +44.2 o d. – 44.2o

  1. Which of the following physical properties differ for each of a pair of enantiomers?

a. solubility in ethanol b. direction of rotation of plane-polarized light c. boiling point and melting point d. index of refraction

  1. Determine the double bond stereochemistry ( E or Z ) for the following molecules.

a. A : E ; B : E b. A : Z ; B : Z c. A : E ; B : Z d. A : Z ; B : E

  1. Determine the double bond stereochemistry ( E or Z ) for the following molecules.

a. A : E ; B : E b. A : Z ; B : Z c. A : E ; B : Z d. A : Z ; B : E

Molecular Structure and Spectra

  1. A strong signal at 1700 cm–1^ in an IR spectrum indicates the presence of a(n)

a. alcohol b. ether c. carbonyl d. amine

  1. A strong signal at 3400 cm–1^ in an IR spectrum indicates the presence of a(n)

a. alcohol b. ether c. carbonyl d. amine

  1. Deduce the structure of an unknown compound with molecular formula C 9 H 10 O using information given by its infrared spectrum.

Intensity (peak): Frequency (cm–1^ ): s 3100 m 2900 m 2800 s 1710 m-w 1600 m-w 1475 m 1465 m 1450 m 1375

a.

b.

c.

d.

  1. Deduce the structure of an unknown compound with molecular formula C 5 H 8 O using information given by its infrared spectrum.

Intensity (peak): Frequency (cm–1^ ): m 3100 m 2800 s 1705 m-w 1640 m 1450 m 1375

a.

b.

c.

d.

  1. Which of the following compounds a–d has an IR absorption at 3300 cm–1^?

a. a b. b c. c d. d

  1. Deduce the structure of an unknown compound using the following 1 H NMR spectrum, mass spectroscopy data, and IR spectrum.

(^1) H NMR spectrum:

δ1.30 (triplet, 6H) δ4.29 (quartet, 4H) δ 7.4–7.9 (multiplet, 4H)

Mass Spectrum: m/e: Intensity: (as % of base peak) 222 10% 177 38% 149 100%

IR Spectrum: Intensity (peak): Frequency (cm–1^ ): s 3100 m 2900 m 2800 s 1740 m-w 1600 m-w 1475 m 1465 m 1450 m 1375 s 1300–

a.

b.

c.

d.

  1. A compound of formula C 5 H 12 gives 1 signal in the 1 H NMR and 2 signals in the 13 C NMR. The compound is

a. pentane. b. 2-methylbutane. c. 2,2-dimethylpropane. d. Cannot tell without more information.

  1. How many methyl peaks would you expect to observe in the 1 H NMR spectrum of cis -1,4-dimethylcyclohexane?

a. 1 b. 2 c. 3 d. 4

  1. The 1 H NMR spectrum of a compound is shown below. What is the structure of the compound?

a.

b.

c.

d.

  1. How many absorption bands will appear in the 13 C NMR spectrum for the following compound?

a. 4 b. 6 c. 7 d. 8

  1. How many absorption bands will appear in the 13 C NMR spectrum for the following compound?

a. 5 b. 7 c. 8 d. 9

  1. Not only the molecular ion peak, but all peaks in the mass spectrum of chlorobenzene are accompanied by a smaller peak one mass unit higher. This peak is due to which of the following?

a. capture of an H atom b. presence of a 13 C c. presence of a 36 Cl d. capture of a proton

  1. What is the exact mass (in atomic mass units: C, 12.0000; H, 1.0078; N, 14.0031; O, 15.9949) of the molecular ion of a compound with molecular formula C 3 H 8 O?

a. 60. b. 60. c. 60. d. 59.

  1. Which of the following cyclohexane conformations has the MOST energy (is the LEAST stable)?

a. chair b. half-chair c. boat d. twist-boat

  1. Which of the following molecules is trans -1, 2-dimethylcyclohexane?

a.

b.

c.

d.

  1. What is the IUPAC name of the following molecule?

a. 1,2-dimethylhexane b. 2,4-dimethylcyclohexane c. Dimethylcyclohexane d. 1,3-dimethylcyclohexane

  1. Which compound has the highest melting point?

a. decane b. 2,2,3,3-tetramethylbutane c. 2,2,3-trimethylpentane d. 4-methylnonane

  1. Which of the following alkanes will have the lowest boiling point?

a.

b.

c.

d.

  1. Which of the following cycloalkanes has the MOST strain energy?

a. cyclobutane b. cyclopentane c. cyclohexane d. cycloheptane

  1. The balanced equation for the combustion of pentane is

a. 4 C 5 H 12 + 2 O 2 → 20 CH 4 + 4 H 2 O b. 2 C 3 H 8 + O 2? → CH 4 + 2 H 2 O c. C 5 H 12 + 8 O 2 → 5 CO 2 + 6 H 2 O d. C 3 H 8 + 5 O 2 → 3 CO 2 + 4 H 2 O

  1. What is the major product of the following reaction?

a.

b.

c.

d.

  1. What is the major product of the following reaction?

a.

b.

c.

d.

  1. Which of the following occurs during the initiation stage of a radical mechanism?

a. Nonradicals are formed from radicals. b. Radicals are formed from other radicals. c. Radicals are formed from nonradicals. d. Nonradicals are formed from other nonradicals.