Concept explainers
a) Bromoacetone
Interpretation:
The structure for bromoacetone is to be shown.
Concept introduction:
To show:
The structure for bromoacetone.
Answer to Problem 54AP
The structure of bromoacetone is
Explanation of Solution
The name indicates that the compound is a ketone with three carbon straight chain with a bromine atom attached to C1.
The structure of bromoacetone is
b) (S)-2-Hydroxypropanal
Interpretation:
The structure for (S)-2-hydroxypropanal is to be shown.
Concept introduction:
To show:
The structure for (S)-2-hydroxypropanal.
Answer to Problem 54AP
The structure of (S)-2-hydroxypropanal is
Explanation of Solution
The name indicates that the compound is an aldehyde with three carbon straight chain with a hydroxyl group attached to C2. The molecule is chiral. The three groups, -OH(first highest priority), -CHO (second highest priority) and -CH3(third highest priority) are arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.
The structure of (S)-2-hydroxypropanal is
c) 2-Methyl-3-heptanone
Interpretation:
The structure for 2-methyl-3-heptanone is to be shown.
Concept introduction:
Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.
To show:
The structure for 2-methyl-3-heptanone.
Answer to Problem 54AP
The structure of 2-methyl-3-heptanone is
Explanation of Solution
The name indicates that the compound is a ketone with seven carbon straight chain having the keto group at position three and a methyl group attached to C2.
The structure of 2-methyl-3-heptanone is
d) (2S,3R)-2,3,4-Trihydroxybutanal
Interpretation:
The structure for (2S,3R)-2,3,4-trihydroxybutanal is to be shown.
Concept introduction:
Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.
To show:
The structure for (2S,3R)-2,3,4-trihydroxybutanal.
Answer to Problem 54AP
The structure of (2S,3R)-2,3,4-trihydroxybutanal is
Explanation of Solution
The name indicates that the compound is an aldehyde with four carbon straight chain and has three hydroxyl groups attached to C2, C3 and C4.
The molecule is chiral. The C2 is attached to the three groups, -OH(first highest priority), -CHO (second highest priority) and –C3 (third highest priority) arranged anticlockwise when viewed from the side away from H (fourth highest priority). Hence it has S stereochemistry.
The C3 is attached to the three groups, -OH(first highest priority), –C2 (second highest priority) and –CH2OH--(third highest priority) arranged clockwise when viewed from the side away from H (fourth highest priority). Hence it has R stereochemistry.
The structure of (2S,3R)-2,3,4-trihydroxybutanal is
e) 2,2,4,4-Tetramethyl-3-pentanone
Interpretation:
The structure for 2,2,4,4-tetramethyl-3-pentanone is to be shown.
Concept introduction:
Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.
To show:
The structure for 2,2,4,4-tetramethyl-3-pentanone.
Answer to Problem 54AP
The structure of 2,2,4,4-tetramethyl-3-pentanone is
Explanation of Solution
The name indicates that the compound is a ketone with five carbon straight chain with a keto group at position three attached to four methyl groups, two on C2 and other two on C4.
The structure of 2,2,4,4-Tetramethyl-3-pentanone is
f) 4-methyl-3-penten-2-one
Interpretation:
The structure for 4-methyl-3-penten-2-one is to be shown.
Concept introduction:
Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.
To show:
The structure for 4-methyl-3-penten-2-one.
Answer to Problem 54AP
The structure of 4-methyl-3-penten-2-one is
Explanation of Solution
The name indicates that the compound is a ketone containing a five carbon straight chain, having a keto group at position two and a double bond between C3 and C4 with a methyl group on C4.
The structure of 4-methyl-3-penten-2-one is
g) Butanedial
Interpretation:
The structure for butanedial is to be shown.
Concept introduction:
Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.
To show:
The structure for butanedial.
Answer to Problem 54AP
The structure of butanedial is
Explanation of Solution
The name of the compound indicates that it has a four carbon straight chain with two aldehyde groups at both ends.
The structure of butanedial is
h) 3-Phenyl-2-propenal
Interpretation:
The structure for 3-phenyl-2-propenal is to be shown.
Concept introduction:
Aldehydes are named by replacing the terminal –e of the parent alkane with –al. The parent chain is the longest one that includes the -CHO group and the –CHO group is numbered as carbon 1. For cyclic alcohols in which the –CHO group is directly attached to the ring, the suffix –carbaldehyde is used.
To show:
The structure for 3-phenyl-2-propenal.
Answer to Problem 54AP
The structure of 3-phenyl-2-propenal is
Explanation of Solution
The name of the compound indicates that the compound is a three carbon aldehyde with a double bond between C2 & C3 and has a phenyl group attached to C3.
The structure of 3-phenyl-2-propenal is
i) 6,6-Dimethyl-2,4-cyclohexadienone
Interpretation:
The structure for 6,6-dimethyl-2,4-cyclohexadienone is to be shown.
Concept introduction:
Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo.
To show:
The structure for 6,6-dimethyl-2,4-cyclohexadienone.
Answer to Problem 54AP
The structure of 6,6-dimethyl-2,4-cyclohexadienone is
Explanation of Solution
The name of the compound indicates that it is a cyclic ketone with a cyclohexadiene ring containing two double bonds, one between C2 & C3 and other between C4 & C5. It also has two methyl groups on C6.
The structure of 6,6-dimethyl-2,4-cyclohexadienone is
j) p-Nitroacetophenone
Interpretation:
The structure for p-nitroacetophenone is to be shown.
Concept introduction:
Ketones are named by replacing the terminal –e of the parent alkane with –one. The parent chain is the longest one that includes the ketone group and the numbering begins at the end nearer to the carbonyl carbon. If other functional groups are present the double bonded oxygen is considered as a substituent on the parent chain with the prefix –oxo. Some common names like acetophenone are retained by IUPAC.
To show:
The structure for p-nitroacetophenone.
Answer to Problem 54AP
The structure of p-nitroacetophenone is
Explanation of Solution
The name of the compound indicates that it contains an actyl and nitro groups attached to a benzene ring in para relationship.
The structure of p-nitroacetophenone is
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Chapter 19 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
- 10. The most important reason why Br- is a better nucleophile than Cl-is ___. A. polarizability; B. size; C. solvation; D. basicity; E. polarity. Please include all steps. Thanks!arrow_forwardPredicting the qualitative acid-base properties of salts Consider the following data on some weak acids and weak bases: base acid Ка K₁₁ name formula name formula nitrous acid HNO2 4.5×10 4 pyridine CHEN 1.7 × 10 9 4 hydrofluoric acid HF 6.8 × 10 methylamine CH3NH2 | 4.4 × 10¯ Use this data to rank the following solutions in order of increasing pH. In other words, select a '1' next to the solution that will have the lowest pH, a '2' next to the solution that will have the next lowest pH, and so on. solution 0.1 M NaNO2 0.1 M KF pH choose one v choose one v 0.1 M C5H5NHBr 0.1 M CH3NH3CI choose one v ✓ choose one 1 (lowest) 2 ☑ 3 4 (highest) 000 18 Ararrow_forward4. The major product from treatment of 2-propanol with the Jonesreagent is ___.A. acetone; B. none of the other answers is correct C. propene; D.propanoic acid; E carbon dioxide. Please include all steps! Thank you!arrow_forward
- 7. All of the following compounds that are at the same oxidation levelare ___.u. methyl epoxide, v. propyne, w. propanal, x. propene,y. 2,2-dihydroxypropane, z. isopropanol?A. u,v,w,y; B. u,v,w; C. v,w,y,z; D. v, z; E. x,y,z Please include all steps. Thank you!arrow_forward9. Which one of the following substituents is the worst leaving group inan SN2 reaction? A. -NH2; B. -OH; C. –F; D. NH3; E. H2O Please include all steps. Thanks!arrow_forwardUsing the general properties of equilibrium constants At a certain temperature, the equilibrium constant K for the following reaction is 2.5 × 105: CO(g) + H2O(g) CO2(g) + H2(g) Use this information to complete the following table. Suppose a 7.0 L reaction vessel is filled with 1.7 mol of CO and 1.7 mol of H2O. What can you say about the composition of the mixture in the vessel at equilibrium? What is the equilibrium constant for the following reaction? Be sure your answer has the correct number of significant digits. CO2(9)+H2(g) CO(g)+H₂O(g) What is the equilibrium constant for the following reaction? Be sure your answer has the correct number of significant digits. 3 CO(g)+3H2O(g) = 3 CO2(g)+3H2(g) There will be very little CO and H2O. x10 There will be very little CO2 and H2. 000 Neither of the above is true. K = ☐ K = ☐ 18 Ararrow_forward
- 8. When ethane thiol is treated with hydrogen peroxide the product is___.A. ethane disulfide; B. diethyl sulfide; C. ethane sulfoxide; D. ethanesulfate; E. ethyl mercaptan. Please include all steps. Thanks!arrow_forward5. The major product of the three step reaction that takes place when 1-propanol is treated with strong acid is?A. dipropyl ether; B. propene; C. propanal; D. isopropyl propyl ether;E. 1-hexanol Please include all steps. Thank you!arrow_forward6. The formula of the product of the addition of HCN to benzaldehydeis ___.A. C8H7NO; B. C8H6NO; C. C14H11NO; D. C9H9NO; E. C9H8NO Please include all steps. Thank you!arrow_forward
- Predicting the qualitative acid-base properties of salts Consider the following data on some weak acids and weak bases: base acid K K a name formula name formula nitrous acid HNO2 4.5×10 hydroxylamine HONH2 1.1 × 10 8 hypochlorous acid HCIO 8 3.0 × 10 methylamine CH3NH2 | 4.4 × 10¯ 4 Use this data to rank the following solutions in order of increasing pH. In other words, select a '1' next to the solution that will have the lowest pH, a '2' next to the solution that will have the next lowest pH, and so on. 0.1 M KCIO solution PH choose one 0.1 M NaNO2 0.1 M CH3NH3Br 0.1 M NaBr choose one ✓ choose one v ✓ choose one 1 (lowest) ☑ 2 3 4 (highest)arrow_forwardFor this Orgo problem, don't worry about question 3 below it. Please explain your thought process, all your steps, and also include how you would tackle a similar problem. Thank you!arrow_forwardUsing the general properties of equilibrium constants At a certain temperature, the equilibrium constant K for the following reaction is 0.84: H2(g) + 2(g) 2 HI(g) = Use this information to complete the following table. Suppose a 34. L reaction vessel is filled with 0.79 mol of HI. What can you say about the composition of the mixture in the vessel at equilibrium? There will be very little H2 and 12. ☐ x10 There will be very little HI. Neither of the above is true. What is the equilibrium constant for the following reaction? Be sure your answer has the correct number of significant digits. 2 HI(g) H₂(9)+12(9) K = What is the equilibrium constant for the following reaction? Be sure your answer has the correct number of significant digits. 2 H2(g)+212(9) 4 HI(g) K = ☐ ☑arrow_forward
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