Washington Signature
[ Search and Navigation ]   [ View Full Site ]
Offices & Services

Offices: Registrar - Catalog

Chemistry

Division of Natural Sciences and Mathematics

 

Aaron Amick, Chair

Dana Chatellier

James Lipchock

Rick Locker

Anne Marteel-Parrish, Deputy Chair

Betsy Moyer-Taylor

Leslie Sherman

 

The mission of the Chemistry Department at Washington College is to provide outstanding undergraduate education in the chemical sciences by integrating classroom instruction with laboratory experimentation, faculty-student collaborative research, and service opportunities. Our goal is to inspire students to become liberally educated scientists. Our program is approved by the American Chemical Society. The program is designed to prepare students for graduate work in pure chemistry, for professional work in other scientific fields such as environmental science, engineering, medicine, dentistry, nursing, pharmacy, neuroscience and veterinary science, for teaching at the secondary school level, and for work in industrial or governmental laboratories. Chemistry graduates have established diverse career paths that range from a dedication to pure or applied scientific research, to management of scientific and business concerns, to consultantships with industries and governments on scientific, environmental, legal, and business issues, and to service as medical personnel and elected public officials.

 

Students who have an interest in majoring in chemistry or double majoring in chemistry and another subject are advised to take CHE 111 and CHE 112 during their first year. Premedical students and students interested in the 3:4 pharmacy program are advised to take CHE 111, 112 and BIO 111, 112 during their first year. Students intending to teach at the secondary school level should consult with the Chair of the Department of Education and the Chair of the Department of Chemistry about planning a full-course schedule as early as possible in their college career. Such students need to be aware that NASDTEC Certification in Chemistry requires BIO 111, 112 and at least one course in computer science.

 

Programs In Chemistry

The Department offers two programs leading to the Bachelor of Science degree in Chemistry: a non-ACS Certified Chemistry major and an ACS Certified Chemistry major. In addition, students may elect to specialize their chemistry major by focusing their elective coursework and Senior Capstone Experience in one of the four areas of emphasis offered by the department (described below). Successful completion of one of these optional areas of emphasis will be noted on a student’s transcript after graduation.

 

 

REQUIREMENTS FOR THE CHEMISTRY MAJOR

 

The table below summarizes the REQUIRED courses for both tracks in chemistry as well as for students who have declared a major in chemistry late (Spring of sophomore year or Fall of junior year).

 

 

Non-ACS certified degree in chemistry

 

ACS certified degree in chemistry

 

Chemistry major declared  late

 

First year

CHE 111, CHE 112

BIO 111*

MAT 201, MAT 202

 

CHE 111, CHE 112

BIO 111*

MAT 201, MAT 202

 

Second year

CHE 201, CHE 202

PHY 111, PHY 112 or PHY 101, PHY 102

 

CHE 201, CHE 202

PHY 111, PHY 112

CHE 111, CHE 112

MAT 201, MAT 202

Third year

CHE 301

CHE 305 or CHE 306

Elective #1 and Elective #2

CHE 392

CHE 301

CHE 305 and CHE 306

CHE 392

CHE Elective #1 and CHE Elective #2

 

CHE 201, CHE 202

PHY 111, PHY 112 or PHY 101, PHY 102

CHE 392

Elective #1 and Elective #2

Fourth year

Elective #3 and Elective #4

CHE SCE

 

CHE 311

CHE 303 or 309

CHE Elective #3

CHE SCE

 

CHE 305 or CHE 306

Elective #3 and Elective #4

CHE SCE

 

 

 

*Students on the pre-med track must take CHE 309 and therefore BIO 111 (BIO 111 is a prerequisite for BIO 409/CHE 309).

 

Elective courses are courses at the 200-level or above. Three of the four elective courses for the non-ACS certified degree can be BIO or PHY courses not counted towards that major. The three elective courses for the ACS certified degree in chemistry must be CHE courses such as: CHE 303 (or CHE 309), CHE 310, CHE 314, CHE 320, CHE 403, CHE 405, CHE 410, CHE 395, 495, CHE 396, 496 or CHE 394, 494.

 

Historically students who obtain a C- or below in the first semester of general chemistry rarely perform well in the second semester of General Chemistry and continue to struggle in Organic Chemistry I and II (CHE 201 and CHE 202). Therefore we recommend that students do not pursue CHE 201 and CHE 202 (Organic Chemistry I, II) if their grade in pre-requisite courses is not satisfactory. We also strongly recommend that students take Organic Chemistry I and II the year immediately following General Chemistry I and II.

 

Areas of Emphasis

In addition to the major offerings listed above, students wishing to specialize within a subdiscipline of chemistry or a chemistry-related cross-disciplinary or multidisciplinary area have the option to complete an area of emphasis within the ACS certified or non-ACS certified chemistry majors. As outlined below, each area of emphasis requires students to complete their SCE in the selected area, as well as three additional 4-credit courses. For students who do not wish to pursue a B.S. in Chemistry with an area of emphasis, they have the option to complete their SCE with any professor of their choice on any topic of their interest.

 

Successful completion of an area of emphasis will be noted on a student’s transcript after graduation. Given that the SCE must be completed in the selected area of emphasis, a student may only complete one area of emphasis. The chemistry department offers the following areas of emphasis:

 

  1. Organic and Medicinal Chemistry

This area of emphasis is designed for students interested in pursuing graduate study or careers in organic chemistry, medicinal chemistry or pharmacology.  Students will gain a strong foundation in organic synthesis and mechanisms, while broadening their knowledge in areas such as drug discovery and pharmacology.

 

Requirements:

SCE specialization in Organic or Medicinal Chemistry, plus three of the following:

  • CHE 403. Advanced Organic Chemistry
  • CHE 320. Introduction to Medicinal Chemistry
  • CHE 494. Advanced Synthesis and Spectroscopy
  • CHE 303 OR CHE 309. Chemistry of Biological Compounds OR Biochemistry

 

  1. Greener Materials Science

This area of emphasis is designed for students interested in receiving a thorough grounding in the basic sciences and engineering of all materials while being exposed to environmentally friendly chemical processes (Green Chemistry). Students will be prepared for graduate study or bench research dealing with the production, structure, characterization, properties, and utilization of metals, ceramics, polymers, composites, nano- and bio-compatible and electronic materials. Additionally future chemists and engineers will be provided the tools required to minimize the environmental impact of materials production.

 

Requirements:

SCE specialization in Greener Materials Science, plus three of the following:

  • CHE 310. Greener and Sustainable Chemistry
  • CHE 311. Inorganic Chemistry
  • CHE 410. Materials Science
  • CHE 494. Advanced Synthesis and Spectroscopy
  • CHE 314. Instrumental Methods of Analysis

 

  1. Physical and Instrumental Chemistry

This area of emphasis is designed for students with an interest in the more physical aspects of chemistry or instrumental design and data analysis. Students will be prepared for graduate school or careers that require a stronger foundation in theoretical or analytical areas of chemistry.

 

Requirements:

SCE specialization in Physical or Instrumental Chemistry, plus three of the following:

  • CHE 305 AND CHE 306. Chemical Thermodynamics and Chemical Dynamics AND Quantum Chemistry and Spectroscopy
  • CHE 314. Instrumental Methods of Analysis
  • CHE 494. Advanced Synthesis and Spectroscopy
  • CHE 405. Biophysical Methods
  • PHY elective at the 200-level or above
  • MAT 203 OR MAT 345. Multivariable Calculus OR Differential Equations

 

  1. Biophysics and Biological Chemistry

This area of emphasis is designed for students interested in pursuing graduate study or a career in biophysics, biological chemistry, chemical biology, pharmacology or related fields. Students will gain a strong background in biomolecular structure and dynamics, techniques utilized in biophysical and biochemical characterization of biomolecules, and principles of effective drug design.

 

Requirements:

SCE specialization in Biophysics or Biological Chemistry, plus three of the following:

  • CHE 303. Chemistry of Biological Compounds
  • CHE 309. Biochemistry
  • CHE 405. Biophysical Methods
  • CHE 320. Introduction to Medicinal Chemistry
  • CHE 305 AND CHE 306. Chemical Thermodynamics and Chemical Dynamics AND Quantum Chemistry and Spectroscopy
  • BIO elective at 200-level or above

 

 

Requirements For The Chemistry Minor

Students intending to minor in Chemistry should meet with the Department Chair early in their career to insure that they are able to complete the following courses and to get their minor declaration card signed.

 

Six chemistry courses are required for the chemistry minor.

CHE 111, 112. General Chemistry I and II

CHE 201, 202. Organic Chemistry I and II

Two courses at the 200 level or above.

 

Chemistry Seminar

All junior majors participate in a one four-credit Chemistry Seminar course offered in the spring semester. This course prepares our chemistry majors to become citizens of the 21st century by exposing them to research ethics, sustainable science literacy, societal and moral issues in chemistry, and academic subject lectures (modern chemistry). Professional preparation (exposure to career options, resume building, job searching and mock interview) as well as improvement of communication skills (oral (debate, discussions, final presentation), written (ethics case study, abstract) and visual (poster, blog) are the main outcomes of this seminar course.

 

Senior Capstone Experience

Chemistry majors fulfill the Senior Capstone Experience by conducting a yearlong research project either based on a laboratory project or an in-depth literature review in collaboration with a chemistry faculty member. Many research projects involve synthetic and preparative procedures and include the use of the department’s research grade analytical instrumentation. The results of this research are presented in the department’s annual research symposium and are included in a written, thesis-quality report. Many projects involve synthetic and preparative procedures and include the use of the department’s research-grade UV-VIS, FTIR, AA, NMR, GC, HPLC, GC-MS, ICP-MS, electrochemical analyzer, and polarimeter. Students pursuing the ACS-certified degree in Chemistry must perform a laboratory-based research project for their SCE to meet the number of laboratory hours required by the ACS. This requirement could be waived if ACS-certified majors have already performed research for credit during the academic year or during the summer. Seniors present the results of their project in a poster session that is open to the College community. The department has a set of Senior Capstone Experience Guidelines that are distributed to both junior and senior chemistry majors each Fall. For those students meeting the College-wide standards of eligibility for departmental honors at graduation, the capstone experience also forms the basis of an oral examination given at the end of the students’ final semester. Students must enroll in CHE SCE in their final semester to obtain credit for the Senior Capstone Experience. The Senior Capstone Experience is graded according to the Washington College grading system, which involves the use of letter grades (A-F) that may be modified by a minus or a plus.

 

 

Internship and Research Opportunities

A number of stipend-bearing internships and research opportunities exist for chemistry majors and minors. Summer on-campus research projects as well as summer and semester-long off-campus internships not only provide additional laboratory experience, but also allow students the opportunity to explore, in depth, areas of chemistry not covered in the core curriculum. Off-campus internships may or may not bear credit. On-campus summer internships are credit bearing.

 

Honors Courses

The Department of Chemistry offers Honors sections of General Chemistry I and General Chemistry II.

 

Distribution Courses

For distribution credit in Natural Sciences, the Chemistry department offers CHE 111, 112 General Chemistry I, II, and CHE 110 Chemistry of the Environment.

 

Advanced Placement Credit

Students scoring 4 or 5 on the chemistry advanced placement examination may, with the approval of the department, receive credit for General Chemistry I, II. Students wishing to progress directly into Organic Chemistry I (CHE 201) must score a 5 on the advanced placement examination and receive approval from the department.

 

Transfer Credit

It is not recommended for Chemistry majors to take any chemistry course off campus. It is not encouraged for any other major to take general chemistry and/or organic chemistry off campus. If absolutely necessary, it is the responsibility of the students to provide the Chair of the Chemistry department the appropriate documentation for transfer credit.

 

NOTE ABOUT PREREQUISITE

Having the correct prerequisite for a course also means that the students successfully pass the prerequisite course. 

 

Course Descriptions

 

  1. (ENV 110) Chemistry of the Environment

This introductory course focuses on the chemical dimensions of current environmental problems such as global warming, ozone depletion, water and soil contamination, and energy production. Fundamental principles of chemical bonding, reactions, and energy are studied as they arise in connection with each environmental issue. Interdisciplinary aspects are explored to further understand the multiple dimensions of the problems. Intended for students planning to major outside the sciences. Three hours of lecture and one hour and 3/4 of laboratory each week. (Offered annually)

 

111, 112. General Chemistry I, II

This two-semester sequence focuses on the fundamental principles of chemistry. Key topics are atomic and molecular structure, chemical bonding, and stoichiometry, with an emphasis on molecules and reactions important in biological systems. Other topics include thermochemistry, kinetics, chemical equilibria, electrochemistry, intermolecular forces and states of matter, periodic properties, coordination chemistry, and an introduction to organic chemistry, biochemistry, and Green Chemistry. Laboratory work is designed to complement lecture material. Three hours of lecture and three hours of laboratory each week. Prerequisite. Chemistry 111 is a prerequisite for Chemistry 112. (Offered annually)

 

201, 202. Organic Chemistry I, II

This two-semester sequence is concerned with the molecular architecture and chemical reactivity of a broad spectrum of organic molecules, including aliphatic and aromatic hydrocarbons, their halogenated derivatives, and molecules containing oxygen and nitrogen, alone or in one or more combinations. Particular emphasis is placed on the structure and function of organic molecules important in biological systems. Heavy emphasis is given to the study of reaction mechanisms. Three hours of lecture and three hours of laboratory each week. Prerequisite. Chemistry 112 or its equivalent. Chemistry 201 is a prerequisite for Chemistry 202. (Offered annually)

 

  1. (ENV 210) Environmental Chemistry

The cycling of natural chemical species and pollutants in the water, soil and air of our earth system is a major component of our complex ecosystem. In this environmental chemistry course, students will develop an understanding of the transport and reactions controlling natural chemical species in our environment, as well as the cycling of pollutants. Students will study current issues of water, soil and air pollution, and how society is working towards reducing the movement of pollutants through our environment. In the laboratory portion of the class, students will investigate the water quality of local water bodies, including the Chester River, as well as conduct hands-on experiments related to the environmental topics studied in class. Three hours of lecture and three hours of laboratory each. Prerequisites. Chemistry 112. (Offered Fall: even numbered years)

 

  1. Analytical Chemistry

This course is intended to be an introduction to analytical chemistry.  Both classical and instrumental methods of analysis are considered.  A detailed treatment of simple and complex chemical equilibria with particular emphasis on theoretical aspects of acid-base, oxidation-reduction, complex formation, and precipitation equilibria is presented as a basis for the classical gravimetric and titrimetric methods.  The instrumental techniques included electroanalytical, uv-visible molecular spectroscopy, atomic spectroscopy, and chromatography.  Applications of the techniques to inorganic, organic, biochemical, and environmental analysis are covered in the lecture and lab components of the course. Three hours of lecture and three hours of laboratory each week. Prerequisite. Chemistry 112. (Offered annually: Fall)

 

  1. Chemistry of Biological Compounds

This course is designed to provide a comprehensive introduction to the structure and function of biological molecules at the molecular level. Using post-translational modification of proteins as a guide, we will explore intermolecular interactions, biomolecular structure (proteins, nucleic acids, carbohydrates and lipids) and fundamental concepts in mechanistic enzymology. Students will learn to interpret biochemical data, predict the impact of mutations associated with disease and visualize biomolecular structures with the aid of computer software commonly utilized in the field. Additional topics include: RNA transcription, protein translation, enzyme engineering and more. Three hours of lecture and three hours of laboratory each week. Prerequisite. Chemistry 202. (Offered annually)

 

  1. Chemical Thermodynamics and Chemical Dynamics

Thermodynamics is the study of the behavior of matter and the transformation between different forms of energy on a macroscopic scale. Chemical dynamics is the study of the rate at which the macroscopic properties and composition of matter change. These changes can involve either transport properties, such as thermal conductivity, viscosity, and diffusion or chemical kinetics. Some of the chemical kinetics topics covered are rate laws, temperature effects on reaction rates, reaction rate theories, reaction mechanisms, and enzyme catalysis. Applications of chemical thermodynamics and chemical dynamics are drawn from environmental chemistry and biochemistry. Laboratory exercises include determination of thermodynamic properties and kinetics experiments. Three hours of lecture and three hours of laboratory each week. Prerequisite: Chemistry 112 and Mathematics 202. Co-requisite: Physics 111. (Offered annually: Fall)

 

  1. Quantum Chemistry and Spectroscopy

Quantum chemistry is the application of quantum mechanics to the field of chemistry. Topics included in the discussion of quantum chemistry are the early development of quantum mechanics, quantum mechanical models for molecular vibrations and rotations, and electronic structure of atoms and molecules. Spectroscopy is the study of the interactions of electromagnetic radiation with matter, and is the principal experimental tool used to investigate the predictions made using quantum mechanics. The laboratory exercises include spectroscopy experiments and the use of molecular modeling programs. Three hours of lecture and three hours of laboratory each week. Prerequisite: Chemistry 112 and Mathematics 202. Co-requisite: Physics 112. (Offered annually: Spring)

 

  1. (BIO 409) Biochemistry

An examination of living systems at the chemical level. Topics will include structure and function of macromolecules, cellular energetics, cellular respiration, and photosynthesis. A laboratory will be conducted weekly to introduce students to experimental techniques. Prerequisite: Biology 111 and Chemistry 202, or permission from instructor. (Offered annually: Fall)

 

  1. Greener and Sustainable Chemistry

Environmentally friendly scientists are increasingly conscious about the need to make chemistry “greener.” The goal of this course is to present a different perspective regarding chemistry and its applications in academia and industry worldwide. This course will cover both the theoretical and practical aspects of green and sustainable chemistry. The introduction will include the foundations of green chemistry and sustainability as well as a description of the tools and principles it employs. There will be an in-depth study concerning the evaluation of methods and tools in designing environmentally benign reactions and chemicals. Real-world examples will be used to illustrate the goals of green chemistry. Throughout the semester students will have the opportunity to enhance their writing and oral presentation skills and improve their communication and discussion abilities. Three hours of lecture each week. Prerequisite: Chemistry 202. (Offered Spring: in rotation with Chemistry 410)

 

  1. Inorganic Chemistry

This course is an in-depth study of structure and bonding in molecules. Topics include atomic structure, symmetry and bond theory, ionic and covalent bonding, coordination and organometallic chemistry, and catalysis. The laboratory work focuses on the synthesis and characterization of the following: main group compounds, bioinorganic molecules, zeolites, coordination and organometallic complexes used in catalysis. It also introduces green inorganic chemistry, computational chemistry, and metal complexes used in bioinorganic chemistry. Three hours of lecture and three hours of laboratory per week. Co-requisite: Chemistry 305 or permission of the instructor. (Offered annually: Fall)

 

  1. Instrumental Methods of Analysis

This course examines instrumental methods based on their selectivity, sensitivity, and detection limits. Instrumental systems are analyzed in terms of electronics, computers, and optics. The following topics are included: Molecular and atomic spectroscopy, electroanalytical techniques, and separation techniques. Applications of the techniques to inorganic, organic, biochemical and environmental analysis are covered in the lecture and lab components of the course. The laboratory emphasizes the critical evaluation of data. Three hours of lecture and three hours of laboratory each week. Prerequisite: Chemistry 201 and Chemistry 301. (Offered annually: Spring)

 

  1. (BIO 409) Biochemistry

An examination of living systems at the chemical level. Topics will include structure and function of macromolecules, cellular energetics, cellular respiration, and photosynthesis. A laboratory will be conducted weekly to introduce students to experimental techniques. Prerequisite: Biology 111 and Chemistry 202, or permission from instructor. (Offered annually: Fall)

 

  1. Introduction to Medicinal Chemistry

This course is an introduction to the field of Medicinal Chemistry and will focus heavily on the chemistry of pharmacological agents as well as their synthesis. Attention will also be placed on enzyme mechanisms and how bioactive molecules affect their activity. This course meets three hours each week. Prerequisite. Chemistry 201 AND 202. (Offered Biennially)

 

  1. Advanced Organic Chemistry

This course expands upon the topics discussed previously in the two semesters of organic chemistry. Topics that are covered are: Frontier Molecular Orbital (FMO) Theory and how this can be applied to chemical reactivity, Pericyclic Reactions, Linear Free-Energy Relationships, Molecular Rearrangements, Heterocyclic Chemistry, and Organometallic Chemistry. Heavy emphasis will be on reaction mechanisms and synthesis.   Prerequisite: Chemistry 202.

 

  1. Biophysical Methods

This course explores experimental methods used to characterize the structure and dynamics of biological molecules. An emphasis will be placed on the theory behind the techniques and the data obtained, in addition to the biological interpretation of the results. Topics include: biomolecule synthesis and purification, NMR spectroscopy, x-ray crystallography, fluorescence spectroscopy, and more. Three hours of lecture each week. Prerequisites: MAT 202 plus CHE 303 or CHE 309.

 

  1. Materials Science

Our lives are influenced by all types of materials in transportation, housing, clothing, communication, recreation, and food production. The development and advancement of societies have been dependent on the ability to use existing materials, produce, manipulate, and select new materials suitable in many technologies that make our existence more comfortable. This course depicts relationships between the processing of a material, its structure, and finally its performance based on its properties in terms of the design, production, and utilization of the material. The overall goal of this course is to become familiar with the selection process that scientists and engineers use when designing a suitable material at a reasonable cost with minimal environmental impact. Three hours of lecture each week. Prerequisite: Chemistry 305 or Chemistry 306 (Offered Spring: in rotation with Chemistry 310)

 

  1. Chemistry Seminar

This seminar course attempts to prepare our Chemistry majors for their future professional career so they become successful professionals and experts in the Chemistry field. It is expected that our majors 1) become proficient at literature searching, reading and interpreting, 2) increase their awareness about societal issues either professionally or as citizens and have the background to constructively engage in debates, 3) understand the variety of career options available to chemists, and 4) are involved in a course relying on critical analysis, decision-making within a context, effective oral, written, and visual communication, and cooperative teamwork. Therefore, at the end of this course, the following “4 Cs” will have been practiced and mastered: Critical thinking and problem solving, Communication, Collaboration, and Creativity and innovation.

 Prerequisite: chemistry major and junior status. (Offered in the Spring)

 

194, 294, 394, 494. Special Topics in Chemistry

A detailed study of an advanced topic or topics in chemistry chosen on the basis of current student interest and faculty expertise. Special topics include but are not limited to: Biophysical Methods, Heterocyclic Chemistry, Organometallic Chemistry, Solid-State Chemistry, Chemistry of Macromolecules, Medicinal Chemistry, Advanced Synthesis and Spectroscopy, and Electronics Instrumentation. Three hours of lecture per week. (Offered annually)

 

195, 295, 395, 495. On-Campus Research

This course is comprised of a ten-week summer research project guided by a faculty mentor. The student and faculty mentor develop a research project supported by a reading list and involving theoretical, laboratory, or field investigations supervised by the faculty mentor. Participants will produce a final report detailing the findings of their research. Students may earn four credits per summer for a maximum of eight credits. Not offered as Pass/Fail. Prerequisite: Permission of the mentor. (Offered annually)

 

196, 296, 396, 496. Off-campus Research

This course consists of an individual research project chosen by the student in consultation with a faculty mentor. The student will, with the help of the mentor, design a project to be implemented during a one- or two-semester period or during the summer. The student will conduct an appropriate literature search, carry out the research, and submit a written report by the end of each semester. Students may earn two credits per semester or four credits for summer research for a maximum of eight credits. Not offered as Pass/Fail. Prerequisite: Permission of the mentor.

 

190, 290, 390, 490. Internship

An internship is based on an opportunity for students to work with industries, governmental laboratories and institutes, and outside non-research based institutions. Students will be able to work closely with an on-site supervisor to discover the numerous aspects of the working world. Participants will produce a final report detailing the findings of their research. Students may earn two or four credits per semester for a maximum of four credits. Not offered as Pass/Fail. Prerequisite: Permission of the mentor. (Offered annually)

 

197, 297, 397, 497. Independent Study

This course provides an opportunity for students to work with a professor of their choice on a research project or on an in-depth literature review project during the academic year. Students may earn one or two credits per semester. Not offered as Pass/Fail. Prerequisite: Permission of the mentor. (Offered annually)

 

SCE. Senior Capstone Experience

Chemistry majors fulfill the Senior Capstone Experience by conducting a yearlong research project in collaboration with a chemistry faculty member and writing a thesis-quality report. Many projects involve synthetic and preparative procedures and include the use of the department’s research-grade UV-VIS, FTIR, AA, NMR, GC, HPLC, GC-MS, ICP-MS, electrochemical analyzer, and polarimeter. Students pursuing the ACS-certified degree in Chemistry must perform a laboratory-based research project for their SCE to meet the number of laboratory hours required by the ACS. This requirement could be waived if ACS-certified majors have already performed research for credit during the academic year or during the summer. Seniors present the results of their project in a poster session that is open to the College community. The Senior Capstone Experience is graded according to the Washington College grading system, which involves the use of letter grades (A-F) that may be modified by a minus or a plus. (Offered annually)